CARBOXYLIC ACID DERIVATIVE-SUBSTITUTED IMINO ARYL COMPOUND, PREPARATION METHOD THEREFOR, HERBICIDAL COMPOSITION AND USE THEREOF

Abstract

 The invention relates to the field of pesticide technology, and in particular a type of carboxylic acid derivative-substituted iminoaryl compound, preparation method, herbicidal composition and use thereof. The compound, as shown in general formula I:

wherein, Q represents

Y represents halogen, haloalkyl or cyano; Z represents halogen; M represents CH or N; W represents OX₅, SX₅ or N(X₅)₂; X represents -CX₁X₂-(alkyl)_n-, -alkyl-CX₁X₂-(alkyl)_n- or -(CH₂)_r-; X₃ and X₄ each independently represent O, S, NH or N-alkyl, etc.. The compound has excellent herbicidal activity against gramineous weeds, broadleaf weeds, cyperaceae weeds and so on even at low application rates, and has high selectivity for crops.

Description

Technical Field

[0001] The invention relates to the field of pesticide technology, and in particular a type of carboxylic acid derivative-substituted iminoaryl compound, preparation method, herbicidal composition and use thereof.

Technical background

[0002] Weed control is one of the most important links in the course of achieving high-efficiency agriculture. Various herbicides are available in the market, for example, patents WO00/50409 etc. disclose the use of a compound of general formula 1-aryl-4-thiotriazine as a herbicide, WO95/06641 discloses a compound of substituted 1-amino-3-phenyluracils with herbicidal activity, WO95/25725 discloses a compound of pyrimidinyl aryl ketone oximes with herbicidal and insecticidal activities. However, the herbicidal properties of these known compounds against harmful plants and their selectivities to crops are not completely satisfactory. And scientists still need to do continuously research and develop new herbicides with high efficacy, safety, economics and different modes of action due to problems such as the growing market, weed resistance, the service life and economics of pesticides as well as people's increasing concern on environment.

Invention contents

[0003] The invention relates to the field of pesticide technology, and in particular a type of carboxylic acid derivative-substituted iminoaryl compound, preparation method, herbicidal composition and use thereof. The compound has excellent herbicidal activity against gramineous weeds, broadleaf weeds, cyperaceae weeds and so on even at low application rates, and has high selectivity for crops.

[0004] The technical solution adopted by the invention is as follows:
A carboxylic acid derivative-substituted iminoaryl compound, represented by general formula I':

[0005] Wherein, the derivative refers to a derivative suitable for agricultural chemistry, which is used to describe the change of the carboxylic acid functional group of the present invention, and it refers to any ester, acylhydrazide, imidate, thioimidate, amidine, amide, orthoester, acyl cyanide, acyl halide, thioester, thionoester, dithiolester, nitrile or any other carboxylic acid derivative well known in the art.

[0006] To be specific, the carboxylic acid derivative-substituted iminoaryl compound, represented by general formula I:

[0007] In the above general formulas I'and I,

Q represents

Y represents halogen, haloalkyl or cyano;

Z represents halogen;

M represents CH or N;

W represents OX₅, SX₅ or N(X₅)₂;

X represents -CX₁X₂-(alkyl)_n-, -alkyl-CX₁X₂-(alkyl)_n- or -(CH₂)_r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkyl carbonyl, alkoxy carbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclic alkyl, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "cycloalkyl", "cycloalkylalkyl", "aryl", "heterocyclyl", "arylalkyl" and "heterocyclic alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

X₃, X₄ each independently represent O, S, NH or N-alkyl;

X₅ represents H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl,





wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, cycloalkenyl, heterocyclyl, aryl,



the "cycloalkyl", "cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

or unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;

Q₁, Q₂, Q₃, Q₄, Q₅ each independently represent O or S;

R₁, R₂ each independently represent H, cyano, alkyl, alkenyl, alkynyl, formyl alkyl, cyanoalkyl, amino, aminoalkyl, amino carbonyl, amino carbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl, R₄R₅N-(CO)-NR₃-,

, R₃-S(O)_m-(alkyl)_n-, R₃-O-(alkyl)_n-, R₃-(CO)-(alkyl)_n-, R₃-O-(alkyl)_n-(CO)-, R₃-(CO)-O-(alkyl)_n-, R₃-S-(CO)-(alkyl)_n-, R₃-O-(CO)-alkyl- or R₃-O-(CO)-O-alkyl-, wherein,

the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen,

the "amino", "aminoalkyl", "amino carbonyl", "amino carbonylalkyl" and "aminosulfonyl" are each independently unsubstituted or substituted by one or two groups selected from -R₁₁, -OR₁₁, -(CO)R₁₁, -(CO)OR₁₁, -alkyl-(CO)OR₁₁, -(SO₂)R₁₁, -(SO₂)OR₁₁, -alkyl-(SO₂)R₁₁, -(CO)N(R₁₂)₂ and -(SO₂)N(R₁₂)₂,

the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₆ represents alkyl, alkenyl, alkynyl or cyano, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, alkoxy and alkoxy carbonyl;

R₇, R₇', R₈, R₈' each independently represent H, alkyl, halogen, haloalkyl, amino, hydroxyalkyl or alkoxy;

X₁₁ independently represents H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl or

wherein, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, alkoxy, alkoxyalkyl, alkyl carbonyl, alkoxy carbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, aryl, arylalkyl, heterocyclyl or heterocyclic alkyl, or C, X₁₃, X₁₄, taken together, form unsubstituted or substituted cyclic structure, or N, X₁₃, X₁₄, taken together, form unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "aryl", "arylalkyl", "heterocyclyl" and "heterocyclic alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₃, R₄, R₅ each independently represent H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₁₁ independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, benzyl, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "phenyl" and "benzyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;

R₁₂ independently represents H, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or N(R₁₂)₂ in -(CO)N(R₁₂)₂ or -(SO₂)N(R₁₂)₂ each independently represents unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;

R₁₃ independently represents H, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;

r represents an integer of 2 or more; m represents 0, 1 or 2; n independently represents 0 or 1.

[0008] Preferably, Y represents halogen, halo C1-C8 alkyl or cyano;

X represents -CX₁X₂-(C1-C8 alkyl)n-, -(C1-C8 alkyl)-CX₁X₂-(C1-C8 alkyl)n- or -(CH₂)_r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halo C1-C8 alkoxy, halo C1-C8 alkylthio, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkoxy C1-C8 alkyl, halo C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, aryl, heterocyclyl, aryl C1-C8 alkyl or heterocyclyl C1-C8 alkyl, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "aryl", "heterocyclyl", "aryl C1-C8 alkyl" and "heterocyclyl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

X₃, X₄ each independently represent O, S, NH or N-(C1-C8)alkyl;

X₅ represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl,



wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl,



the "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

or heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;

R₁, R₂ each independently represent H, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino, amino C1-C8 alkyl, amino carbonyl, amino carbonyl C1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, R₄R₅N-(CO)-NR₃-,

, R₃-S(O)_m-(C1-C8 alkyl)_n-, R₃-O-(C1-C8 alkyl)_n-, R₃-(CO)-(C1-C8 alkyl)n-, R₃-O-(C1-C8 alkyl)_n-(CO)-, R₃-(CO)-O-(C1-C8 alkyl)n-, R₃-S-(CO)-(C1-C8 alkyl)n-, R₃-O-(CO)-(C1-C8 alkyl)- or R₃-O-(CO)-O-(C1-C8 alkyl)-, wherein,

the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen,

the "amino", "amino C1-C8 alkyl", "amino carbonyl", "amino carbonyl C1-C8 alkyl" and "aminosulfonyl" are each independently unsubstituted or substituted by one or two groups selected from -R₁₁, -OR₁₁, -(CO)R₁₁, -(CO)OR₁₁, -(C1-C8 alkyl)-(CO)OR₁₁, -(SO₂)R₁₁, -(SO₂)OR₁₁, -(C1-C8 alkyl)-(SO₂)R₁₁, -(CO)N(R₁₂)₂ and -(SO₂)N(R₁₂)₂,

the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₆ represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl or cyano, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkoxy and C1-C8 alkoxy carbonyl;

R₇, R₇', R₈, R₈' each independently represent H, C1-C8 alkyl, halogen, halo C1-C8 alkyl, amino, hydroxy C1-C8 alkyl or C1-C8 alkoxy;

X₁₁ independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl or

, wherein, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or C, X₁₃, X₁₄, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl, or N, X₁₃, X₁₄, taken together, form heterocyclyl with nitrogen atom at 1-position, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl", "aryl C1-C8 alkyl", "heterocyclyl" and "heterocyclyl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring, the "5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl" is unsubstituted or substituted by 1-4 groups selected from C1-C8 alkyl, C1-C8 alkoxy carbonyl and benzyl, or together with aryl or heterocyclyl forms a fused ring, the "heterocyclyl with nitrogen atom at 1-position"is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;

R₃, R₄, R₅ each independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₁₁ independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, benzyl, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "phenyl" and "benzyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;

R₁₂ independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or N(R₁₂)₂ in -(CO)N(R₁₂)₂ or -(SO₂)N(R₁₂)₂ independently represents heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;

R₁₃ independently represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;

r represents 2, 3, 4, 5 or 6.

[0009] More preferably, Y represents halogen, halo C1-C6 alkyl or cyano;

X represents -CX₁X₂-(C1-C6 alkyl)n-, -(C1-C6 alkyl)-CX₁X₂-(C1-C6 alkyl)n- or -(CH₂)_r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C6 alkyl, halo C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, aryl, heterocyclyl, aryl C1-C6 alkyl or heterocyclyl C1-C6 alkyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "aryl", "heterocyclyl", "aryl C1-C6 alkyl" and "heterocyclyl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

X₃, X₄ each independently represent O, S, NH or N-(C1-C6)alkyl;

X₅ represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,



wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,



, the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

or heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

R₁, R₂ each independently represent H, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino, amino C1-C6 alkyl, amino carbonyl, amino carbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, R₄R₅N-(CO)-NR₃-,

R₃-S(O)_m-(C1-C6 alkyl)_n-, R₃-O-(C1-C6 alkyl)_n-, R₃-(CO)-(C1-C6 alkyl)n-, R₃-O-(C1-C6 alkyl)_n-(CO)-, R₃-(CO)-O-(C1-C6 alkyl)n-, R₃-S-(CO)-(C1-C6 alkyl)n-, R₃-O-(CO)-(C1-C6 alkyl)- or R₃-O-(CO)-O-(C1-C6 alkyl)-, wherein,

the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen,

the "amino", "amino C1-C6 alkyl", "amino carbonyl", "amino carbonyl C1-C6 alkyl" and "aminosulfonyl" are each independently unsubstituted or substituted by one or two groups selected from -R₁₁, -OR₁₁, -(CO)R₁₁, -(CO)OR₁₁, -(C1-C6 alkyl)-(CO)OR₁₁, -(SO₂)R₁₁, -(SO₂)OR₁₁, -(C1-C6 alkyl)-(SO₂)R₁₁, -(CO)N(R₁₂)₂ and -(SO₂)N(R₁₂)₂,

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₆ represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyano, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, C1-C6 alkoxy and C1-C6 alkoxy carbonyl;

R₇, R₇', R₈, R₈' each independently represent H, C1-C6 alkyl, halogen, halo C1-C6 alkyl, amino, hydroxy C1-C6 alkyl or C1-C6 alkoxy;

X₁₁ independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl or

wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃,

-(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, or C, X₁₃, X₁₄, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl, or N, X₁₃, X₁₄, taken together, form heterocyclyl

with nitrogen atom at 1-position, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl", "aryl C1-C6 alkyl", "heterocyclyl" and "heterocyclyl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring, the "5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl" is unsubstituted or substituted by 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy carbonyl and benzyl, or together with aryl or heterocyclyl forms a fused ring, the



are unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

R₃, R₄, R₅ each independently represent H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₁₁ independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, benzyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "phenyl" and "benzyl"are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy;

R₁₂ independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or N(R₁₂)₂ in -(CO)N(R₁₂)₂ or -(SO₂)N(R₁₂)₂ independently represents heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

R₁₃ independently represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl or phenyl substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy.

[0010] Still more preferably, X represents -CX₁X₂-(C1-C3 alkyl)_n-, -(C1-C3 alkyl)-CX₁X₂-(C1-C3 alkyl)n- or -(CH₂)_r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C3 alkyl, hydroxy C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C3 alkyl, halo C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylamino C1-C3 alkyl, aryl, heterocyclyl, aryl C1-C3 alkyl or heterocyclyl C1-C3 alkyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "aryl", "heterocyclyl", "aryl C1-C3 alkyl" and "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

X₅ represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,



wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,



, the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

or heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

X₁₁ independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl or

wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", "heterocyclyl C1-C3 alkyl", "aryl" and "aryl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", "heterocyclyl C1-C3 alkyl", "aryl" and "aryl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or C, X₁₃, X₁₄, taken together, form 5~8 membered saturated carbocyclyl,

or N, X₁₃, X₁₄, taken together, form heterocyclyl

with nitrogen atom at 1-position, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl", "aryl C1-C3 alkyl", "heterocyclyl" and "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring, the "5~8 membered saturated carbocyclyl,

is unsubstituted or substituted by 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy carbonyl and benzyl, or together with phenyl or thienyl forms a fused ring, the

are unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl.

[0011] Further more preferably, Q represents

[0012] In the definition of the compound represented by the above Formula and all of the following structural formulas, the technical terms used, whether used alone or used in compound word, represent the following substituents: an alkyl having more than two carbon atoms may be linear or branched. For example, the alkyl in the compound word "-alkyl-(CO)OR₁₁" may be -CH₂-, -CH₂CH₂-, -CH(CH₃)-, -CH₂CH₂CH₂-, -C(CH₃)₂-, and the like; "-(CH₂)_r-" may be -CH₂CH₂-, -CH₂CH₂CH₂-, and the like. The alkyl is, for example, C₁ alkyl: methyl; C₂ alkyl: ethyl; C₃ alkyl: propyl such as n-propyl or isopropyl; C₄ alkyl: butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; C₅ alkyl: pentyl such as n-pentyl; C₆ alkyl: hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, the alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butyl-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. The alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bond(s) may be placed at any position of each unsaturated group. The cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, the cycloalkenyl is monocycloalkenyl having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bond can be at any position. Halogen is fluorine, chlorine, bromine or iodine.

[0013] Unless otherwise specified, the "aryl" of the present invention includes, but is not limited to, phenyl, naphthyl,

the "heterocyclyl" not only includes, but is not limited to, saturated or unsaturated non-aromatic cyclic group,





etc., but also includes, but is not limited to,"heteroaryl", which is an aromatic cyclic group having, for example, 3 to 6 ring atoms and optionally being fused with a benzo ring, and 1 to 4 (for example, 1, 2 , 3 or 4) heteroatoms of the ring are selected from the group consisting of oxygen, nitrogen and sulfur. For example,

[0014] If a group is substituted by a group, which should be understood to mean that the group is substituted by one or more groups, which are same or different groups, selected from the mentioned groups. In addition, the same or different substitution characters contained in the same or different substituents are independently selected, and may be the same or different. This is also applicable to ring systems formed with different atoms and units. Meanwhile, the scope of the claims will exclude those compounds chemically unstable under standard conditions known to those skilled in the art.

[0015] In addition, unless specifically defined, the term occurring before or after multiple juxtaposed substituents (separated by "," or "or") in the present invention has a limiting effect on each of the substituents, such as the wording "unsubstituted or halogen-substituted" in the term "unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O-" has a limiting effect on each group "-OCH₂CH₂-" "-OCH₂O-" occurring thereafter; "alkylamino" refers to the amino group which is monosubstituted or disubstituted by alkyl, other substituted amino groups are similarly defined; a group (including heterocyclyl, aryl, etc.) without being specified a linking site may be attached at any site, including a C or N site; if it is substituted, the substituent may be substituted at any site as long as it comply with the valence bond theory. For example, if the heteroaryl

is substituted with one methyl, it can be

etc..

[0016] It should be pointed out that, when the carbon atom (C^∗) connected to X₁ and X₂ in the general formula is a chiral center (i.e., X₁ and X₂ are not the same), it is in R configuration or S configuration, preferably R configuration, and based on the content of stereoisomers having R and S configurations at this position, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), still more preferably 90-100% (R), still more preferably 95-100% (R). Wherein, "stereochemical purity" means the amount of the stated stereoisomer expressed as a percentage of the total amount of stereoisomers having the given chiral centre.

[0017] In the present invention the stereochemical configuration at the marked ^∗ position of formula I is fixed as being predominantly (R) according to the Cahn-Ingold-Prelog system, however is the subject matter of the invention is also directed to all stereoisomers at other locants which are encompassed by formula I, and their mixtures. Such compounds of the formula I contain, e.g. one or more additional asymmetric carbon atoms or else double bonds which are not stated specifically in the formula I. It will be understood that the present invention embraces both the pure isomers and more or less enriched mixtures thereof, where the asymmetric carbon atom in marked ^∗ position is in the R-configuration or, in mixtures, a compound or compounds of same chemical constitution have the R-configuration in marked ^∗ position or are present in a ratio that compounds having the R-configuration are predominantly present (at least 60% R-configuration) whilst the other asymmetric carbon atom(s) may be present in racemic form or are more or less resolved too. Provided the condition for the stereochemical configuration at marked ^∗ position is met, the possible stereoisomers which are defined by their specific spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by formula I and can be obtained by customary methods from mixtures of the stereoisomers, or else be prepared by stereoselective reactions in combination with the use of stereochemically pure raw materials.

[0018] The invention also encompasses any keto and enol tautomer forms and mixtures and salts thereof, if respective functional groups are present.

[0019] Stereoisomers can be obtained by optical resolution from the mixture obtained in the preparation. The stereoisomers may also be prepared selectively by using stereoselective reactions and using optically active raw materials and/or auxiliaries.It is generally possible to use customary methods for optical resolutions (cf. Textbooks of Stereochemistry), for example following processes for separating mixtures into diastereomers, for example physical processes, such as crystallization, chromatographic processes, in particular column chromatography and high pressure liquid chromatography, distillation, if appropriate under reduced pressure, extraction and other processes, it is possible to separate the remaining mixtures of enantiomers, generally by chromatographic separation on chiral solid phases. Suitable for preparative amounts or use on an industrial scale are processes such as the crystallization of diastereomeric salts which can be obtained from the compounds (I) using optically active acids and, if appropriate, provided that acidic groups are present, using optically active bases.

[0020] A method for preparing the carboxylic acid derivative-substituted iminoaryl compound is provided, which comprises the following steps:

subjecting a compound represented by general formula II and a compound represented by general formula III' to an elimination reaction to obtain a compound represented by general formula I', with the chemical reaction equation shown as follows:

or, subjecting a compound represented by general formula II and a compound represented by general formula III to an elimination reaction to obtain a compound represented by general formula I, with the chemical reaction equation shown as follows:

wherein, Hal represents halogen, other substituents Q, M, W, Y, Z, X, X₃ and X₄ are as defined above;

preferably, the reaction is carried out in the presence of a base and a solvent.

[0021] The base is at least one selected from inorganic bases (such as K₂CO₃, Na₂CO₃, Cs₂CO₃, NaHCO₃, KF, CsF, KOAc, AcONa, K₃PO₄, t-BuONa, EtONa, NaOH, KOH, NaOMe and the like) and organic bases (such as pyrazole, triethylamine, DIEA and the like).

[0022] The solvent is at least one selected from DMF, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane and ethyl acetate.

[0023] In addition, when Q represents

the target product can also be prepared by firstly preparing the intermediate product



through the above method, and then performing conventional substitution reaction with R₆-Hal (Hal represents halogen, R₆ represents alkyl, alkenyl, alkynyl, or haloalkyl).

[0024] The present invention also provides a herbicidal composition, comprising (i) at least one of the carboxylic acid derivative-substituted iminoaryl compounds in a herbicidally effective amount; (component A); preferably, further comprising (ii) one or more other herbicides (component B) in a herbicidally effective amount and/or safeners; more preferably, further comprising (iii) a formulation auxiliary accepted in agricultural chemistry.

[0025] In a specific embodiment, the other herbicide is one or more selected from the following compounds and acids, salts and esters thereof:

(1) HPPD inhibitor selected from: topramezone(CAS NO.: 210631-68-8), isoxaflutole(CAS NO.: 141112-29-0), tembotrione(CAS NO.: 335104-84-2), tefuryltrione(CAS NO.: 473278-76-1), shuangzuocaotong(CAS NO.: 1622908-18-2), huanbifucaotong(CAS NO.: 1855929-45-1), sanzuohuangcaotong(CAS NO.: 1911613-97-2), benzuofucaotong(CAS NO.: 1992017-55-6), and

(2) PDS inhibitor selected from: flurtamone (CAS NO.: 96525-23-4), diflufenican (CAS NO.: 83164-33-4), and picolinafen (CAS NO.: 137641-05-5);

(3) DOXP inhibitor selected from: clomazone (CAS NO.: 81777-89-1), and bixlozone (CAS NO.: 81777-95-9);

(4) ALS inhibitor selected from: tribenuron-methyl(CAS NO.: 101200-48-0), thifensulfuron methyl(CAS NO.: 79277-27-3), pyrazosulfuron-ethyl(CAS NO.: 93697-74-6), thiencarbazone-methyl(CAS NO.: 317815-83-1), halosulfuron methyl(CAS NO.: 100784-20-1), rimsulfuron(CAS NO.: 122931-48-0), nicosulfuron(CAS NO.: 111991-09-4), and imazamox(CAS NO.: 114311-32-9);

(5) ACCase inhibitor selected from: clethodim (CAS NO.: 99129-21-2), sethoxydim (CAS NO.: 74051-80-2), and quizalofop-P-methyl (CAS NO.: 100646-51-3);

(6) PPO inhibitor selected from: oxyfluorfen(CAS NO.: 42874-03-3), oxadiazon(CAS NO.: 19666-30-9), oxadiargyl(CAS NO.: 39807-15-3), sulfentrazone(CAS NO.: 122836-35-5), pyraclonil(CAS NO.: 158353-15-2), flumioxazin(CAS NO.: 103361-09-7), saflufenacil(CAS NO.: 372137-35-4), carfentrazone-ethyl(CAS NO.: 128639-02-1), and trifludimoxazin(CAS NO.: 1258836-72-4);

(7) PSII inhibitor selected from: metribuzin(CAS NO.: 21087-64-9), terbuthylazine(CAS NO.: 5915-41-3), amicarbazone(CAS NO.: 129909-90-6), chlorotoluron(CAS NO.: 15545-48-9), isoproturon(CAS NO.: 34123-59-6), bromacil(CAS NO.: 314-40-9), propanil(CAS NO.: 709-98-8), desmedipham(CAS NO.: 13684-56-5), phenmedipham(CAS NO.: 13684-63-4), bentazone(CAS NO.: 25057-89-0), and bromoxynil(CAS NO.: 1689-84-5);

(8) inhibitor of microtubule assembly selected from: butralin (CAS NO.: 33629-47-9), and pendimethalin (CAS NO.: 40487-42-1);

(9) VLCFA inhibitor selected from: butachlor (CAS NO.: 23184-66-9), pretilachlor (CAS NO.: 51218-49-6), mefenacet (CAS NO.: 73250-68-7), s-metolachlor (CAS NO.: 87392-12-9), flufenacet (CAS NO.: 142459-58-3), pyroxasulfone (CAS NO.: 447399-55-5), and anilofos (CAS NO.: 764249-01-0);

(10) lipid synthesis (non-acetyl-CoA carboxylase) inhibitor: prosulfocarb (CAS NO.: 52888-80-9);

(11) Synthetic hormone inhibitor selected from:

, fluroxypyr(CAS NO.: 69377-81-7), florpyrauxifen benzyl(CAS NO.: 1390661-72-9), halauxifen-methyl(CAS NO.: 943831-98-9), triclopyr(CAS NO.: 55335-06-3), clopyralid(CAS NO.: 1702-17-6), picloram(CAS NO.: 1918-02-1), aminopyralid(CAS NO.: 150114-71-9), dicamba(CAS NO.: 1918-00-9), 2-methyl-4-chlorophenoxyacetic acid(CAS NO.: 94-74-6), and 2,4-dichlorophenoxy acetic acid(CAS NO.: 94-75-7);

(12) EPSPS inhibitor: glyphosate (CAS NO.: 1071-83-6);

(13) GS inhibitor selected from: glufosinate ammonium (CAS NO.: 77182-82-2), and glufosinate-P-ammonium (CAS NO.: 35597-44-5);

(14) PSI inhibitor selected from: paraquat dichloride (CAS NO.: 1910-42-5), and diquat dibromide monohydrate (CAS NO.: 2764-72-9);

(15) Cellulose synthesis inhibitor selected from: triaziflam (CAS NO.: 131475-57-5), and indaziflam (CAS NO.: 950782-86-2);

(16) others: cinmethylin (CAS NO.: 87818-31-3).

[0026] In the context of the present specification, if an abbreviation of a generic name of an active compound is used, it includes in each case all customary derivatives, such as esters and salts, as well as isomers, in particular optical isomers, especially one or more commercially available forms. If the generic name denotes an ester or a salt, it also includes in each case all other conventional derivatives, such as other esters and salts, free acids and neutral compounds, as well as isomers, in particular optical isomers, especially one or more commercially available forms. The chemical name given to a compound means at least one compound encompassed by the generic name, and generally the preferred compound. In the case of sulfonamides such as sulfonylurea, salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group.

[0027] Wherein, the active ingredient A to the active ingredient B in the herbicidal composition is in a weight ratio of 1:1000~1000:1, 1:800~800:1 or 1:600~600:1, preferably 1:500~500:1, 1:400~400:1 or 1:300~300:1, more preferably 1:200~200:1, 1:100~100:1 or 1:80~80:1, further preferably 1:50~50:1, 1:30~30:1, 1:20~20:1, 1:10~10:1, 1:5~1:1 or 1:1~5:1. In some embodiments, the active ingredients A and B together account for 1-95%, preferably 10-80%, of the total weight of the herbicidal composition.

[0028] The safener is selected from one or more of isoxadifen-ethyl (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), mefenpyr-diethyl (CAS: 135590-91-9), cloquintocet-mexyl (CAS: 99607-70-2), gibberellic acid (CAS: 77-06-5), furilazole (CAS: 121776-33-8), and metcamifen (CAS: 129531-12-0).

[0029] The preparation adjuvant comprises, for example, a carrier and/or a surfactant.

[0030] The term "carrier" herein refers to an organic or inorganic, natural or synthetic substance, which facilitates the application of the active ingredients. In general, the carrier is inert and must be agriculturally acceptable, especially is acceptable to a plant to be treated. The carrier may be a solid, such as clay, a natural or synthetic silicate, silica, a resin, a wax, a solid fertilizer and so on; or a liquid such as water, an alcohol, a ketone, a petroleum fraction, an aromatic or paraffinic hydrocarbon, a chlorohydrocarbon, liquefied gas and so on.

[0031] The surfactant, which may be ionic or non-ionic, can include an emulsifier, a dispersant or a wetting agent. Examples which may be mentioned are a salt of polyacrylic acid, a salt of lignosulfonic acid, a salt of phenolsulfonic acid or of naphthalenesulfonic acid, a polymer of ethylene oxide with an aliphatic alcohol or with an aliphatic acid or with an aliphatic amine or with a substituted phenol (in particular, an alkylphenol or an arylphenol), a sulfosuccinate, a taurine derivative (especially an alkyl taurate) and a phosphoric ester of an alcohol or of a polyhydroxyethylated phenol, an alkyl sulfonate, an alkylaryl sulfonate, an alkyl sulfate, a laurylether sulfate, a fatty alcohol sulfate, a sulfated hexadecanol, heptadecanol and octadecanol and a sulfated fatty alcohol polyglycol ether, and further include a condensate of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, a polyethylene glycol alkylphenyl ether, a polyethylene glycol tributylphenyl ether, a polyethylene glycol tristearylphenyl ether, a alkylaryl polyether alcohol, an alcohol and fatty alcohol/ethylene oxide condensate, ethoxylated castor oil, a polyoxyethylene alkyl ether, an ethoxylated polyoxypropylene, a lauryl alcohol polyglycol ether acetal, a sorbitol ester, a lignin sulfite waste liquid, a protein, a denatured protein, a polysaccharide (e.g., methylcellulose), a hydrophobic modified starch, a polyvinyl alcohol, a polycarboxylate, a polyalkoxylate, a polyvinylamine, a polyvinylpyrrolidone, and a copolymer thereof. At least one surfactant may be required to facilitate dispersion of the active ingredient in water and proper application thereof to a plant.

[0032] The composition can also comprise various other components, such as a protective colloid, an adhesive, a thickener, a thixotropic agent, a penetrant, a stabilizer, a chelating agent, a dye, a colorant or a polymer.

[0033] The composition of the present invention may be diluted prior to use or used directly by users. The compositon can be prepared through a conventional processing method, that is, the active ingredient(s) is mixed with a liquid solvent or a solid carrier, and then one or more of the surfactants such as a dispersant, a stabilizer, a wetting agent, an adhesive, or a defoaming agent, etc. are added.

[0034] The herbicidal composition may be in a form of a formulation which is selected from: a dispersible oil suspension, a water suspension, a suspoemulsion, a wettable powder, an emulsifiable concentrate, a water-dispersible granule (a dry suspension), an aqueous emulsion and a microemulsion.

[0035] In short, the composition of the present invention can be mixed with solid and liquid additives conventionally used in formulations of the prior art. As the external conditions change, the amount of active ingredients used is also different. The external conditions are, for example, temperature, humidity, the nature of the herbicide used, etc. It can have a large variation range, for example between 0.001 and 1.0 kg/ha, or more active substances, but preferably between 0.005 and 750 g/ha, especially between 0.005 and 500 g/ha.

[0036] A method for controlling an undesirable plant is provided, which comprises applying at least one of the carboxylic acid derivative-substituted iminoaryl compounds or the herbicidal composition in a herbicidally effective amount on a plant or in its area or to soil or water to control the emergence or growth of undesirable plant.

[0037] Use of at least one of the carboxylic acid derivative-substituted iminoaryl compounds or the herbicidal composition for controlling a undesirable plant; preferably, the carboxylic acid derivative-substituted iminoaryl compound is used to control a weed in a useful crop, the useful crop is a genetically modified crop or a crop treated by genome editing technique.

[0038] The compounds of the formula I according to the invention have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants (undesirable plants). The active compounds also act efficiently on perennial weeds which produce shoots from rhizomes, root stocks or other perennial organs and which are difficult to control. In this context, it is generally immaterial whether the substances are applied pre-sowing, pre-emergence or post-emergence. Specifically, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without these being a restriction to certain species. Examples of weed species on which the active compounds act efficiently are, from amongst the monocotyledons, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species from the annual sector and from amongst the perennial species Agropyron, Cynodon, Imperata and Sorghum, and also perennial Cyperus species.

[0039] In the case of the dicotyledonous weed species, the spectrum of action extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon from amongst the annuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds. The active compounds according to the invention also effect outstanding control of harmful plants which occur under the specific conditions of rice growing such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. If the compounds according to the invention are applied to the soil surface prior to germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely. If the compounds according to the invention are applied to the soil surface prior to germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely. In particular, the compounds according to the invention exhibit excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor and against Amaranthus, Galium and Kochia species.

[0040] The undesirable plants also include herbicide-resistant or tolerant weed species.

[0041] Although the compounds according to the invention have an excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, rice, corn, sugarbeet, cotton and soya, are not damaged at all, or only to a negligible extent. In particular, they have excellent compatibility in cereals, such as wheat, barley and corn, in particular wheat. For these reasons, the present compounds are highly suitable for selectively controlling undesirable plant growth in plantings for agricultural use or in plantings of ornamentals.

[0042] Owing to their herbicidal properties, these active compounds can also be employed for controlling harmful plants in crops of known or still to be developed genetically engineered plants. The transgenic plants generally have particularly advantageous properties, for example resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the quantity, quality, storage-stability, composition and to specific ingredients of the harvested product. Thus, transgenic plants having an increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested produce are known.

[0043] The use of the compounds of the formula I according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereal, such as wheat, barley, rye, oats, millet, rice, maniok and corn, or else in crops of sugarbeet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species is preferred. The compounds of the formula I can preferably be used as herbicides in crops of useful plants which are resistant or which have been made resistant by genetic engineering toward the phytotoxic effects of the herbicides.

[0044] Conventional ways for preparing novel plants which have modified properties compared to known plants comprise, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants having modified properties can be generated with the aid of genetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0 131 624). For example, there have been described several cases of:

• genetically engineered changes in crop plants in order to modify the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806),
• transgenic crop plants which are resistant to certain herbicides of the glufosinate- (cf., for example, EP-A 0 242 236, EP-A 0 242 246) or glyphosate-type (WO 92/00377), or of the sulfonylurea-type (EP-A 0 257 993, U.S. Pat. No. 5,013,659A),
• transgenic crop plants, for example cotton, having the ability to produce Bacillus thuringiensis toxins (Bt toxins) which impart resistance to certain pests to the plants (EP-A 0 142 924, EP-A 0 193 259),
• transgenic crop plants having a modified fatty acid composition (WO 91/13972).

[0045] Numerous molecular biological techniques which allow the preparation of novel transgenic plants having modified properties are known in principle; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition 1996, or Christou, "Trends in Plant Science" 1 (1996) 423-431). In order to carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molecules into plasmids which allow a mutagenesis or a change in the sequence to occur by recombination of DNA sequences. Using the abovementioned standard processes it is possible, for example, to exchange bases, to remove partial sequences or to add natural or synthetic sequences. To link the DNA fragments with each other, it is possible to attach adaptors or linkers to the fragments.

[0046] Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.

[0047] To this end it is possible to employ both DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences that may be present, and DNA molecules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but which are not entirely identical.

[0048] When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of the plant cells. However, to achieve localization in a certain compartment, it is, for example, possible to link the coding region with DNA sequences which ensure localization in a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

[0049] The transgenic plant cells can be regenerated to whole plants using known techniques. The transgenic plants can in principle be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants. In this manner, it is possible to obtain transgenic plants which have modified properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

[0050] When using the active compounds according to the invention in transgenic crops, in addition to the effects against harmful plants which can be observed in other crops, there are frequently effects which are specific for the application in the respective transgenic crop, for example a modified or specifically broadened spectrum of weeds which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crops are resistant, and an effect on the growth and the yield of the transgenic crop plants. The invention therefore also provides for the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

[0051] In addition, the substances according to the invention have outstanding growth-regulating properties in crop plants. They engage in the plant metabolism in a regulating manner and can this be employed for the targeted control of plant constituents and for facilitating harvesting, for example by provoking desiccation and stunted growth. Furthermore, they are also suitable for generally regulating and inhibiting undesirable vegetative growth, without destroying the plants in the process. Inhibition of vegetative growth plays an important role in many monocotyledon and dicotyledon crops because lodging can be reduced hereby, or prevented completely.

[0052] The compounds according to the invention can be applied in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also provides herbicidal compositions comprising compounds of the formula I. The compounds of the formula I can be formulated in various ways depending on the prevailing biological and/or chemico-physical parameters. Examples of suitable formulation options are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil dispersions (OD), oil- or water-based dispersions, oil-miscible solutions, dusts (DP), capsule suspensions (CS), seed-dressing compositions, granules for broadcasting and soil application, granules (GR) in the form of microgranules, spray granules, coating granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

[0053] The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflüchenaktive Äthylenoxidaddkte" [Surface-active ethylene oxide adducts], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

[0054] Wettable powders are preparations which are uniformly dispersible in water and which contain, in addition to the active compound and as well as a diluent or inert substance, surfactants of ionic and/or nonionic type (wetting agents, dispersants), for example polyethoxylated alkyl phenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutyinaphthalenesulfona-te or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatus such as hammer mills, fan mills and air-jet mills, and are mixed simultaneously or subsequently with the formulation auxiliaries.

[0055] Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatic compounds or hydrocarbons or mixtures of the solvents, with the addition of one or more surfactants of ionic and/or nonionic type (emulsifiers). Examples of emulsifiers which can be used are calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

[0056] Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet milling using commercially customary bead mills, with or without the addition of surfactants as already mentioned above, for example, in the case of the other formulation types.

[0057] Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if desired, surfactants as already mentioned above, for example, in the case of the other formulation types.

[0058] Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active-compound concentrates to the surface of carriers such as sand, kaolinites or granulated inert material, by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner which is customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers. Water-dispersible granules are generally prepared by the customary processes, such as spray-drying, fluidized-bed granulation, disk granulation, mixing using high-speed mixers, and extrusion without solid inert material.

[0059] For the preparation of disk, fluidized-bed, extruder and spray granules, see for example processes in "Spray-Drying Handbook" 3rd ed. 1979, G Goodwin Ltd., London; J. E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff.; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products, see for example G C. Klingman, "Weed Control as a Science", John Wiley and Sons Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0060] The agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula I. In wettable powders the concentration of active compound is, for example, from about 10 to 99% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates the concentration of active compound can be from about 1 to 90%, preferably from 5 to 80%, by weight. Formulations in the form of dusts contain from 1 to 30% by weight of active compound, preferably most commonly from 5 to 20% by weight of active compound, while sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50%, by weight of active compound. In the case of water-dispersible granules the content of active compound depends partly on whether the active compound is in liquid or solid form and on the granulation auxiliaries, fillers, etc. that are used. In water-dispersible granules the content of active compound, for example, is between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0061] In addition, the formulations of active compound may comprise the tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity regulators which are customary in each case.

[0062] Based on these formulations it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a ready-mix or tank mix.

[0063] Suitable active compounds which can be combined with the active compounds according to the invention in mixed formulations or in a tank mix are, for example, known active compounds as described in for example World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and in the literature cited therein. For example the following active compounds may be mentioned as herbicides which can be combined with the compounds of the formula I (note: the compounds are either named by the "common name" in accordance with the International Organization for Standardization (ISO) or by the chemical names, if appropriate together with a customary code number): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, ethachlor, napropamide, R-left handed napropamide, propanil, mefenacet, diphenamid, diflufenican, ethaprochlor, beflubutamid, bromobutide, dimethenamid, dimethenamid-P, etobenzanid, flufenacet, thenylchlor, metazachlor, isoxaben, flamprop-M-methyl, flamprop-M-propyl, allidochlor, pethoxamid, chloranocryl, cyprazine, mefluidide, monalide, delachlor, prynachlor, terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor, clomeprop, propyzamide, pentanochlor, carbetamide, benzoylprop-ethyl, cyprazole, butenachlor, tebutam, benzipram, mogrton, dichlofluanid, naproanilide, diethatyl-ethyl, naptalam, flufenacet, EL-177, benzadox, chlorthiamid, chlorophthalimide, isocarbamide, picolinafen, atrazine, simazine, prometryn, cyanatryn, simetryn, ametryn, propazine, dipropetryn, SSH-108, terbutryn, terbuthylazine, triaziflam, cyprazine, proglinazine, trietazine, prometon, simetone, aziprotryne, desmetryn, dimethametryn, procyazine, mesoprazine, sebuthylazine, secbumeton, terbumeton, methoprotryne, cyanatryn, ipazine, chlorazine, atraton, pendimethalin, eglinazine, cyanuric acid, indaziflam, chlorsulfuron, metsulfuron-methyl, bensulfuron methyl, chlorimuron-ethyl, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, iodosulfuron-methyl sodium, foramsulfuron, cinosulfuron, triasulfuron, sulfometuron methyl, nicosulfuron, ethametsulfuron-methyl, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, azimsulfuron, flazasulfuron, monosulfuron, monosulfuron-ester, flucarbazone-sodium, flupyrsulfuron-methyl, halosulfuron-methyl, oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, sodium metsulfuron methyl, flucetosulfuron, HNPC-C, orthosulfamuron, propyrisulfuron, metazosulfuron, acifluorfen, fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlornitrofen, aclonifen, ethoxyfen-ethyl, bifenox, nitrofluorfen, chlomethoxyfen, fluorodifen, fluoronitrofen, furyloxyfen, nitrofen, TOPE, DMNP, PPG1013, AKH-7088, halosafen, chlortoluron, isoproturon, linuron, diuron, dymron, fluometuron, benzthiazuron, methabenzthiazuron, cumyluron, ethidimuron, isouron, tebuthiuron, buturon, chlorbromuron, methyldymron, phenobenzuron, SK-85, metobromuron, metoxuron, afesin, monuron, siduron, fenuron, fluothiuron, neburon, chloroxuron, noruron, isonoruron, 3-cyclooctyl-1, thiazfluron, tebuthiuron, difenoxuron, parafluron, methylamine tribunil, karbutilate, trimeturon, dimefuron, monisouron, anisuron, methiuron, chloreturon, tetrafluron, phenmedipham, phenmedipham-ethyl, desmedipham, asulam, terbucarb, barban, propham, chlorpropham, rowmate, swep, chlorbufam, carboxazole, chlorprocarb, fenasulam, BCPC, CPPC, carbasulam, butylate, benthiocarb, vernolate, molinate, triallate, dimepiperate, esprocarb, pyributicarb, cycloate, avadex, EPTC, ethiolate, orbencarb, pebulate, prosulfocarb, tiocarbazil, CDEC, dimexano, isopolinate, methiobencarb, 2,4-D butyl ester, MCPA-Na, 2,4-D isooctyl ester, MCPA isooctyl ester, 2,4-D sodium salt, 2,4-D dimethyla mine salt, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high 2,4-D propionic acid salt, 2,4-D butyric acid, MCPA propionic acid, MCPA propionic acid salt, MCPA butyric acid, 2,4,5-D, 2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine salt, dicamba, erbon, chlorfenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-ethy, fenoxaprop-p-ethyl, propaquizafop, cyhalofop-butyl, metamifop, clodinafop-propargyl, fenthiaprop-ethyl, chloroazifop-propynyl, poppenate-methyl, trifopsime, isoxapyrifop, paraquat, diquat, oryzalin, ethalfluralin, isopropalin, nitralin, profluralin, prodinamine, benfluralin, fluchloraline, dinitramina, dipropalin, chlornidine, methalpropalin, dinoprop, glyphosate, anilofos, glufosinate ammonium, amiprophos-methyl, sulphosate, piperophos, bialaphos-sodium, bensulide, butamifos, phocarb, 2,4-DEP, H-9201, zytron, imazapyr, imazethapyr, imazaquin, imazamox, imazamox ammonium salt, imazapic, imazamethabenz-methyl, fluroxypyr, fluroxypyr isooctyl ester, clopyralid, picloram, trichlopyr, dithiopyr, haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid, diflufenzopyr, triclopyr-butotyl, Cliodinate, sethoxydim, clethodim, cycloxydim, alloxydim, clefoxydim, butroxydim, tralkoxydim, tepraloxydim, buthidazole, metribuzin, hexazinone, metamitron, ethiozin, ametridione, amibuzin, bromoxynil, bromoxynil octanoate, ioxynil octanoate, ioxynil, dichlobenil, diphenatrile, pyraclonil, chloroxynil, iodobonil, flumetsulam, florasulam, penoxsulam, metosulam, cloransulam-methyl, diclosulam, pyroxsulam, benfuresate, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, benzobicylon, mesotrione, sulcotrione, tembotrione, tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone, fenoxasulfone, methiozolin, fluazolate, pyraflufen-ethyl, pyrazolynate, difenzoquat, pyrazoxyfen, benzofenap, nipyraclofen, pyrasulfotole, topramezone, pyroxasulfone, cafenstrole, flupoxam, aminotriazole, amicarbazone, azafenidin, carfentrazone-ethyl, sulfentrazone, bencarbazone, benzfendizone, butafenacil, bromacil, isocil, lenacil, terbacil, flupropacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, propyzamide, MK-129, flumezin, pentachlorophenol, dinoseb, dinoterb, dinoterb acetate, dinosam, DNOC, chloronitrophene, medinoterb acetate, dinofenate, oxadiargyl, oxadiazon, pentoxazone, Flufenacet, fluthiacet-methyl, fentrazamide, flufenpyr-ethyl, pyrazon, brompyrazon, metflurazon, kusakira, dimidazon, oxapyrazon, norflurazon, pyridafol, quinclorac, quinmerac, bentazone, pyridate, oxaziclomefone, benazolin, clomazone, cinmethylin, ZJ0702, pyribambenz-propyl, indanofan, sodium chlorate, dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, flupropanate, cyperquat, bromofenoxim, epronaz, methazole, flurtamone, benfuresate, ethofumesate, tioclorim, chlorthal, fluorochloridone, tavron, acrolein, bentranil, tridiphane, chlorfenpropmethyl, thidiarizonaimin, phenisopham, busoxinone, methoxyphenone, saflufenacil, clacyfos, chloropon, alorac, diethamquat, etnipromid, iprymidam, ipfencarbazone, thiencarbazone-methyl, pyrimisulfan, chlorflurazole, tripropindan, sulglycapin, prosulfalin, cambendichlor, aminocyclopyrachlor, rodethanil, benoxacor, fenclorim, flurazole, fenchlorazole-ethyl, cloquintocet-mexyl, oxabetrinil, MG/91, cyometrinil, DKA-24, mefenpyr-diethyl, furilazole, fluxofenim, isoxadifen-ethyl, dichlormid, halauxifen-methyl, DOW florpyrauxifen, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

[0064] For use, the formulations which are present in commercially available form are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Products in the form of dusts, granules for soil application or broadcasting and sprayable solutions are usually not further diluted with other inert substances prior to use. The application rate of the compounds of the formula I required varies with the external conditions, such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha or more of active substance, but it is preferably between 0.005 and 750 g/ha, especially between 0.005 and 250g/ha.

Specific Mode for Carrying out the Invention

[0065] The following embodiments are used to illustrate the present invention in detail and should not be taken as any limit to the present invention. The scope of the invention would be explained through the Claims.

[0066] In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table 1 and Table A. The structure and information of a certain compound are shown in Table 1 and Table A. The compounds in Table 1 and Table A are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

[0067] Table A is constructed in the same way as that of Table 1 above, except for replacing the racemate compounds having a chiral center (

wherein, X represents -C^∗X₁X₂-(alkyl)_n-, -alkyl-C^∗X₁X₂-(alkyl)_n-, that is, X₁, X₂ are not the same, the carbon atom at ^∗ is the chiral center) (that is, compounds 1-188, 193-432, 438-439, 441-469, 471-478, 481-484, 486-493, 495-545, 547-641, 644-669, 672, 674-681, 683-727, 729-829, 832-857, 860, 862-869, 871-916, 918-1018, 1021-1046, 1049, 1051-1058 and 1060-1069) with the corresponding compounds in R configuration and deleting the compounds having no chiral center at the corresponding position, and in Table A, the entries in the column "No." are listed in sequence as "1(R)-188(R), 193(R)-432(R), 438(R)-439(R), 441(R)-469(R), 471(R)-478(R), 481(R)-484(R), 486(R)-493(R), 495(R)-545(R), 547(R)-641(R), 644(R)-669(R), 672(R), 674(R)-681(R), 683(R)-727(R), 729(R)-829(R), 832(R)-857(R), 860(R), 862(R)-869(R), 871(R)-916(R), 918(R)-1018(R), 1021(R)-1046(R), 1049(R), 1051(R)-1058(R) and 1060(R)-1069(R)". For example, "1(R)" corresponds to R configuration of compound "1" in Table 1, "194(R)" corresponds to R configuration of compound "194" in Table 1.

[0068] The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route have been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the preparation method of the present invention is included in the scope of the present invention. In addition, the following preparation method can be further modified according to the disclosures of the present invention by using common chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.

[0069] The following method of application can be used to improve further understanding of the preparation method of the present invention. The specific material, class and condition have been determined to be further explication of the present invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.

[0070] Examples of representative compounds are as follows, the synthesis methods of other compounds are similar, and will not be described in detail here.

1. Synthesis of compound 1

[0071] 

1) 1-1 (10 g, 49.1 mmol, 1.0 eq), Fe powder (8.23 g, 147.4 mmol, 3.0 eq), NH₄Cl (5.26 g, 98.3 mmol, 2.0 eq) and water (50 ml) were added to 500 ml of EtOH solution in sequence. Then, the reaction solution was reacted at 80°C for 1 hour. LCMS test showed the disappearance of raw materials. After filtration, the solution was concentrated to remove ethanol and then extracted with ethyl acetate. The organic phase was washed with saturated brine (100ml^∗1), and then concentrated to obtain 1-2 (12 g, crude product) (black solid).

2) 1-2 (12 g, 69.1 mmol, 1.0 eq, crude product) was added to 100 ml of toluene solution. Then, 1-3 (10.8 g, 69.1 mmol, 1.0 eq) was added to the reaction solution at 100°C. After the addition was completed, the reaction solution was reacted at 100°C for 1 hour. LCMS test showed the disappearance of raw materials, and the generation of a product. The reaction solution was concentrated to remove toluene. The resulting crude product was separated by column chromatography to obtain 1-4 (5g) (yellow solid).

3) 1-5 (3.8 g, 17.0 mmol, 1.0 eq) and AcONa (0.7 g, 8.5 mmol, 0.5 eq) were added to 50 ml of DMF solution. Then, 1-4 (5 g, 17.0 mmol, 1.0 eq) was added to the reaction solution at 60°C. After the addition was completed, the reaction solution was reacted at 60°C for 1 hour. LCMS test showed the disappearance of raw materials, and the occurrence of new peak. After the addition of water (50ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (100ml^∗1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 1-6 (4.0 g, 71.3% yield) (white solid).

4) 1-6 (4 g, 12.1 mmol, 1.0 eq) was added to 40 ml of EtOH, and then NH₂OHHCl (0.93 g, 13.3 mmol, 1.1 eq) aqueous solution (6 ml) was added dropwise to the reaction solution at 0°C. After the addition was completed, the reaction solution was stirred at 0°C for 2 hours. LCMS test showed that the raw materials were almost consumed, and one major new peak occurred. The reaction solution was concentrated to remove a part of ethanol and then poured into 10 ml of water, causing a solid to precipitate out. After filtration, the filter cake was washed with water and dried to obtain 1-7 (7 g, 71.7% yield) (white solid).

5) 1-7 (0.2 g, 0.58 mmol, 1.0 eq), a (0.14 g, 1.1 mmol, 2 eq) and K₂CO₃ (0.24 g, 1.74 mmol, 3 eq) were added to 5 mL of DMF solution in sequence. Then, the reaction solution was reacted at room temperature for 4 hours. LCMS test showed the disappearance of raw materials, and there were all product peaks. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml^∗1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 1 (0.15 g, 60 % yield) (white solid).

2. Synthesis of compound 1(R) configuration

[0072] 

1-7 (0.2 g, 0.58 mmol, 1.0 eq), b (0.14 g, 1.1 mmol, 2 eq), K₂CO₃ (0.24 g, 1.74 mmol, 3 eq) were added to 5 mL of DMF solution in sequence. Then, the reaction solution was reacted at room temperature for 4 hours. LCMS test showed the disappearance of raw materials, and there were all product peaks. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml^∗1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 1(R) (0.15 g, 60% yield, R/S=98/2) (white solid).

3. Synthesis of compound 194(R)

[0073] 

1) 1-1 (20 g, 98.3 mmol, 1.0 eq) was added to 200 ml of EtOH, and then NH₂OHHCl (7.5 g, 108.1 mmol, 1.1 eq) aqueous solution (30 ml) was added dropwise to the reaction solution at 0°C. After the addition was completed, the reaction solution was stirred at 0°C for 3 hours. LCMS test showed that the raw materials were almost consumed and one major new peak occurred. The reaction solution was concentrated to remove a part of ethanol and then poured into 100 ml of water, causing a solid to precipitate out. After filtration, the filter cake was washed with water and dried to obtain 194-1 (20 g, 93% yield) (white solid).

2) 194-1 (5 g, 22.9 mmol, 1.0 eq), Fe powder (3.8 g, 68.6 mmol, 3 eq), NH₄Cl (2.5 g, 45.8 mmol, 2 eq) and water (10ml) were added to 50 ml of EtOH in sequence. Then, the reaction solution was reacted at 80°C for 1 hour. LCMS test showed the occurrence of product peak. The reaction solution was filtered with celite and then concentrated to remove ethanol. After the addition of water (20ml), the reaction solution was extracted with ethyl acetate and then concentrated to obtain a black crude product. The crude product was separated and purified by column chromatography to obtain 194-2 (2 g, 46.4% yield) (gray solid).

3) 194-2 (1 g, 5.3 mmol, 1.0 eq) and c (1.1 g, 5.3 mmol, 1.0 eq) were added to 20 ml of acetic acid, and the reaction solution was reacted at 110°C for 1 hour. LCMS test showed that the reaction of raw materials was basically completed, and there was one major product peak. The reaction solution was concentrated to remove the solvent. The resulting crude product was separated by column chromatography to obtain 194-3 (1.5 g, 80.5% yield) (white solid).

4) 194-3 (0.4 g, 1.1 mmol, 1.5 eq), b (0.18 g, 1.5 mmol, 1.3 eq) and K₂CO₃ (0.2 g, 1.5 mmol, 1.3 eq) were added to 8 ml of DMF in sequence. Then, the reaction solution was reacted at 25°C for 4 hours. LCMS test showed the generation of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml^∗1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 194-4 (0.3 g, 60.2% yield) (white solid).

5) 194-4 (0.3 g, 0.69 mmol, 1.0 eq), MeI (0.13 g, 0.9 mmol, 1.3 eq) and K₂CO₃ (0.12 g, 0.9 mmol, 1.3 eq) were added to 6 ml of DMF in sequence. Then, the reaction solution was reacted at 25°C for 2 hours. LCMS test showed the generation of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (10ml^∗1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 194(R) (0.2 g, 64.6% yield, R/S=99/1) (white solid).

4. Synthesis of compound 504

[0074] 

(1) 504-1 (2 g, 1.0 eq), DessMartin (4.8 g, 2 eq) were added to 50 ml of DCM solution. Then, the reaction solution was reacted at room temperature for 2 hours. LCMS test showed the completion of reaction. After the addition of NaHCO₃ aqueous solution (100ml), the reaction solution was extracted with DCM. The organic phase was washed with saturated brine (100ml^∗2), and then concentrated. The resulting crude product was separated by column chromatography to obtain 504-2 (1.6 g, 82% yield) (white solid).

(2) 504-2 (1.6 g, 1.0 eq), water (10 ml), hydroxylamine hydrochloride (0.63 g, 2 eq) were added to 30 ml of ethanol solution. Then, the reaction solution was reacted at room temperature for 2 hours. LCMS test showed the completion of reaction. The reaction solution was concentrated. The resulting crude product was separated by column chromatography to obtain 504-3 (1.1 g, 69% yield) (white oil).

(3) 504-3 (0.3 g, 1.0 eq) and K₂CO₃ (170 mg, 1.5 eq) were added to 10 ml of DMF, then a (150 mg, 1.5 eq) was added to the reaction solution at 25°C, followed by reacting at 25°C for 8 hours. LCMS test showed the generation of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (20ml^∗1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 504 (0.2 g, 54% yield) (white solid).

5. Synthesis of compound 919

[0075] 

(1) 919-1 (0.3 g, 1.0 eq) and NH₂NH₂H₂O (0.5 g, 85% aqueous solution, 10 eq) were added to 10 ml of THF. Then, the reaction solution was stirred at 60°C for 3 hours. LCMS test showed the generation of a product. The reaction solution was concentrated. The resulting crude product was separated by column chromatography to obtain 919-2 (0.15 g, 48%yield) (white solid).

(2) 919-2 (0.15 g, 1.0 eq) and K₂CO₃ (74 mg, 1.3 eq) were added to 6 ml of DMF, then a (55 mg, 1.1 eq) was added to the reaction solution at 25°C, followed by reacting at 25°C for 8 hours. LCMS test showed the generation of a product. After the addition of water (10ml), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated brine (20ml^∗1), and then concentrated. The resulting crude product was separated by column chromatography to obtain 919 (50 mg, 27% yield) (white solid).

Biological activity evaluation:

[0076] The activity level criteria for plant damage (i.e., growth control rate) are as follows:

Level 5: growth control rate is above 85%;

Level 4: growth control rate is greater than or equal to 60% and less than 85%;

Level 3: growth control rate is greater than or equal to 40% and less than 60%;

Level 2: growth control rate is greater than or equal to 20% and less than 40%;

Level 1: growth control rate is greater than or equal to 5% and less than 20%;

Level 0: growth control rate is less than 5%.

[0077] The above growth control rates are fresh weight control rates.

Experiment on weeding effect in post-emergence stage:

[0078] Monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Abutilon theophrasti, Galium aparine, Stellaria media, Lithospermum arvense, rorippa indica, Alopecurus aequalis, Alopecurus japonicus, Eleusine indica, Beckmannia syzigachne, Sclerochloa dura, Conyza Canadensis, Phleum paniculatum, Veronica didyma Tenore, Bromus japonicus, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodiaceae, Commelina communis, Sonchus arvensis, Convolvulus arvensis, Cirsium setosum, Bidens tripartita L., Solanum nigrum, Acalypha australis, Digitaria sanguinalis, Echinochloa crusgalli, Setaria viridis, Setaria glauca, Leptochloa chinensis, Monochoria vaginalis, Sagittaria trifolia, Scirpus juncoides, Cyperus rotundus, Cyperus iria, Cyperus difformis, Fimbristylis, Portulaca oleracea, Xanthium sibiricum, Pharbitis nil, etc.) and major crop seeds (wheat, corn, rice, soybean, cotton, oilseed rape, millet, sorghum, potato, sesame, ricinus, etc.) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated in the 2-3 leaf stage. The tested compounds of the present invention were respectively dissolved in acetone, then added with Tween 80 and 1.5 liter/ha of emulsifiable concentrate of methyl oleate as synergist, diluted with a certain amount of water to obtain a solution with a certain concentration, and sprayed with a spray tower onto the plants. After the application, the plants were cultured for 3 weeks in the greenhouse, and then the experimental results of the weeding were counted. The doses of the used compounds were 500, 250, 125, 60, 30, 15, 7.5g/ha, and the averages were obtained by repeating for three times. Representative data are listed in Table 2.

Table 2. Results on weeding effect in post-emergence stage

Compound NO.	Digitaria sanguinalis	Echinochloa crusgalli	Setaria viridis	Eleusine indica	Alopecurus japonicus	Abutilon theophrasti	Dose
1	5	5	5	5	5	5	15g/ha
1(R)	5	5	5	5	5	5	15g/ha
2	5	5	5	5	5	5	15g/ha
2(R)	5	5	5	5	5	5	15g/ha
3	5	5	5	5	4	5	15g/ha
3(R)	5	5	5	5	4	5	15g/ha
4	5	5	5	5	5	5	15g/ha
4(R)	5	5	5	5	5	5	15g/ha
5	5	5	5	5	5	5	15g/ha
5(R)	5	5	5	5	5	5	15g/ha
6	5	5	5	5	5	5	15g/ha
6(R)	5	5	5	5	5	5	15g/ha
9	5	5	5	5	5	5	15g/ha
9(R)	5	5	5	5	5	5	15g/ha
10	5	5	5	5	5	5	15g/ha
10(R)	5	5	5	5	5	5	15g/ha
11	5	5	5	5	5	5	15g/ha
11(R)	5	5	5	5	5	5	15g/ha
12	5	5	5	5	5	5	15g/ha
12(R)	5	5	5	5	5	5	15g/ha
14	5	5	5	5	4	5	15g/ha
14(R)	5	5	5	5	4	5	15g/ha
17	5	5	5	5	5	5	15g/ha
17(R)	5	5	5	5	5	5	15g/ha
20	5	5	5	5	5	5	15g/ha
20(R)	5	5	5	5	5	5	15g/ha
24	5	5	5	5	5	5	15g/ha
24(R)	5	5	5	5	5	5	15g/ha
26	5	5	5	5	5	5	15g/ha
26(R)	5	5	5	5	5	5	15g/ha
42	5	5	5	5	4	5	15g/ha
42(R)	5	5	5	5	4	5	15g/ha
59	5	5	5	5	N	5	15g/ha
59(R)	5	5	5	5	4	5	15g/ha
60	5	5	5	5	4	5	15g/ha
60(R)	5	5	5	5	4	5	15g/ha
72	5	5	5	5	4	5	15g/ha
72(R)	5	5	5	5	5	5	15g/ha
74	4	5	5	4	N	5	15g/ha
74(R)	4	5	5	5	N	5	15g/ha
76	5	5	5	5	5	5	15g/ha
76(R)	5	5	5	5	5	5	15g/ha
80	5	5	5	5	5	5	15g/ha
80(R)	5	5	5	5	5	5	15g/ha
83	4	5	5	5	4	5	15g/ha
83(R)	4	5	5	5	4	5	15g/ha
84	4	5	5	5	4	5	15g/ha
84(R)	4	5	5	5	4	5	15g/ha
85	5	5	5	5	N	5	15g/ha
85(R)	5	5	5	5	4	5	15g/ha
86	3	4	4	5	3	5	15g/ha
86(R)	3	4	4	5	3	5	15g/ha
87	5	5	5	5	5	5	15g/ha
87(R)	5	5	5	5	5	5	15g/ha
88	5	5	5	5	5	5	15g/ha
88(R)	5	5	5	5	5	5	15g/ha
124	5	5	5	5	4	5	15g/ha
124(R)	5	5	5	5	5	5	15g/ha
161	4	5	5	5	4	5	15g/ha
161(R)	4	5	5	5	4	5	15g/ha
164	5	5	5	5	5	5	15g/ha
164(R)	5	5	5	5	5	5	15g/ha
168	5	5	5	5	5	5	15g/ha
168(R)	5	5	5	5	5	5	15g/ha
183	5	5	5	5	5	5	15g/ha
183(R)	5	5	5	5	5	5	15g/ha
189	4	4	5	5	4	5	15g/ha
193	5	5	5	5	5	5	15g/ha
193(R)	5	5	5	5	5	5	15g/ha
194	5	5	5	5	5	5	15g/ha
194(R)	5	5	5	5	5	5	15g/ha
194	5	5	5	5	4	5	7.5g/ha
194(R)	5	5	5	5	5	5	7.5g/ha
196	5	5	5	5	5	5	15g/ha
196(R)	5	5	5	5	5	5	15g/ha
198	5	5	5	5	5	5	15g/ha
198(R)	5	5	5	5	5	5	15g/ha
199	5	5	5	5	5	5	15g/ha
199(R)	5	5	5	5	5	5	15g/ha
200	5	5	5	5	5	5	15g/ha
200(R)	5	5	5	5	5	5	15g/ha
201	5	5	5	5	5	5	15g/ha
201(R)	5	5	5	5	5	5	15g/ha
202	5	5	5	5	5	5	15g/ha
202(R)	5	5	5	5	5	5	15g/ha
203	5	5	5	5	5	5	15g/ha
203(R)	5	5	5	5	5	5	15g/ha
204	5	5	5	5	5	5	15g/ha
204(R)	5	5	5	5	5	5	15g/ha
205	5	5	5	5	5	5	15g/ha
205(R)	5	5	5	5	5	5	15g/ha
206	5	5	5	5	5	5	15g/ha
206(R)	5	5	5	5	5	5	15g/ha
207	5	5	5	5	5	5	15g/ha
207(R)	5	5	5	5	5	5	15g/ha
208	5	5	5	5	5	5	15g/ha
208(R)	5	5	5	5	5	5	15g/ha
209	5	5	5	5	5	5	15g/ha
209(R)	5	5	5	5	5	5	15g/ha
212	5	5	5	5	5	5	15g/ha
212(R)	5	5	5	5	5	5	15g/ha
214	5	5	5	5	5	5	15g/ha
214(R)	5	5	5	5	5	5	15g/ha
216	5	5	5	5	4	5	15g/ha
216(R)	5	5	5	5	4	5	15g/ha
217	5	5	5	5	5	5	15g/ha
217(R)	5	5	5	5	5	5	15g/ha
218	5	5	5	5	5	5	15g/ha
218(R)	5	5	5	5	5	5	15g/ha
220	5	5	5	5	5	5	15g/ha
220(R)	5	5	5	5	5	5	15g/ha
221	5	5	5	5	4	5	15g/ha
221(R)	5	5	5	5	5	5	15g/ha
225	5	5	5	5	4	5	15g/ha
225(R)	5	5	5	5	5	5	15g/ha
226	5	5	5	5	5	5	15g/ha
226(R)	5	5	5	5	5	5	15g/ha
227	5	5	5	5	5	5	15g/ha
227(R)	5	5	5	5	5	5	15g/ha
228	5	5	5	5	5	5	15g/ha
228(R)	5	5	5	5	5	5	15g/ha
230	5	5	5	5	5	5	15g/ha
230(R)	5	5	5	5	5	5	15g/ha
231	5	5	5	5	5	5	15g/ha
231(R)	5	5	5	5	5	5	15g/ha
232	5	5	5	5	5	5	15g/ha
232(R)	5	5	5	5	5	5	15g/ha
233	5	5	5	5	5	5	15g/ha
233(R)	5	5	5	5	5	5	15g/ha
234	5	5	5	5	5	5	15g/ha
234(R)	5	5	5	5	5	5	15g/ha
236	5	5	5	5	5	5	60g/ha
236(R)	5	5	5	5	5	5	60g/ha
238	5	5	5	5	5	5	15g/ha
238(R)	5	5	5	5	5	5	15g/ha
239	5	5	5	5	5	5	15g/ha
239(R)	5	5	5	5	5	5	15g/ha
240	5	5	5	5	5	5	30g/ha
240(R)	5	5	5	5	5	5	30g/ha
241	5	5	5	5	5	5	30g/ha
241(R)	5	5	5	5	5	5	30g/ha
243	5	5	5	5	5	5	15g/ha
243(R)	5	5	5	5	5	5	15g/ha
245	5	5	5	5	5	5	30g/ha
245(R)	5	5	5	5	5	5	30g/ha
246	5	5	5	5	5	5	15g/ha
246(R)	5	5	5	5	5	5	15g/ha
248	5	5	5	5	5	5	15g/ha
248(R)	5	5	5	5	5	5	15g/ha
249	5	5	5	5	5	5	15g/ha
249(R)	5	5	5	5	5	5	15g/ha
250	5	5	5	5	5	5	15g/ha
250(R)	5	5	5	5	5	5	15g/ha
251	5	5	5	5	5	5	15g/ha
251(R)	5	5	5	5	5	5	15g/ha
252	5	5	5	5	5	5	15g/ha
252(R)	5	5	5	5	5	5	15g/ha
253	5	5	5	5	5	5	15g/ha
253(R)	5	5	5	5	5	5	15g/ha
254	5	5	5	5	5	5	15g/ha
254(R)	5	5	5	5	5	5	15g/ha
255	5	5	5	5	5	5	30g/ha
255(R)	5	5	5	5	5	5	30g/ha
258	5	5	5	5	4	5	15g/ha
258(R)	5	5	5	5	4	5	15g/ha
259	5	5	5	5	5	5	30g/ha
259(R)	5	5	5	5	5	5	30g/ha
262	5	5	5	5	5	5	15g/ha
262(R)	5	5	5	5	5	5	15g/ha
263	5	5	5	5	5	5	60g/ha
263(R)	5	5	5	5	5	5	60g/ha
264	5	5	5	5	5	5	15g/ha
264(R)	5	5	5	5	5	5	15g/ha
266	5	5	5	5	5	5	30g/ha
266(R)	5	5	5	5	5	5	30g/ha
268	5	5	5	5	5	5	30g/ha
268(R)	5	5	5	5	5	5	30g/ha
283	5	5	5	5	5	5	15g/ha
283(R)	5	5	5	5	5	5	15g/ha
284	5	5	5	5	5	5	15g/ha
284(R)	5	5	5	5	5	5	15g/ha
285	5	5	5	5	5	5	30g/ha
285(R)	5	5	5	5	5	5	30g/ha
286	5	5	5	5	5	5	30g/ha
286(R)	5	5	5	5	5	5	30g/ha
301	5	5	5	5	5	5	15g/ha
301(R)	5	5	5	5	5	5	15g/ha
302	5	5	5	5	5	5	15g/ha
302(R)	5	5	5	5	5	5	15g/ha
303	5	5	5	5	5	5	15g/ha
303(R)	5	5	5	5	5	5	15g/ha
313	5	5	5	5	5	5	15g/ha
313(R)	5	5	5	5	5	5	15g/ha
315	5	5	5	5	5	5	15g/ha
315(R)	5	5	5	5	5	5	15g/ha
316	5	5	5	5	5	5	15g/ha
316(R)	5	5	5	5	5	5	15g/ha
318	5	5	5	5	5	5	15g/ha
318(R)	5	5	5	5	5	5	15g/ha
319	5	5	5	5	5	5	30g/ha
319(R)	5	5	5	5	5	5	30g/ha
321	5	5	5	5	5	5	120g/ha
321(R)	5	5	5	5	5	5	120g/ha
322	5	5	5	5	5	5	120g/ha
322(R)	5	5	5	5	5	5	120g/ha
331	5	5	5	5	5	5	15g/ha
331(R)	5	5	5	5	5	5	15g/ha
333	5	5	5	5	5	5	15g/ha
333(R)	5	5	5	5	5	5	15g/ha
337	5	5	5	5	5	5	15g/ha
337(R)	5	5	5	5	5	5	15g/ha
342	5	5	5	5	4	5	15g/ha
342(R)	5	5	5	5	5	5	15g/ha
344	5	5	5	5	5	5	15g/ha
344(R)	5	5	5	5	5	5	15g/ha
347	5	5	5	5	5	5	30g/ha
347(R)	5	5	5	5	5	5	30g/ha
349	5	5	5	5	5	5	15g/ha
349(R)	5	5	5	5	5	5	15g/ha
351	5	5	5	5	5	5	60g/ha
351(R)	5	5	5	5	5	5	60g/ha
388	5	5	5	5	4	5	15g/ha
388(R)	5	5	5	5	5	5	15g/ha
390	5	5	5	5	5	5	15g/ha
390(R)	5	5	5	5	5	5	15g/ha
391	5	5	5	5	5	5	60g/ha
391(R)	5	5	5	5	5	5	60g/ha
392	5	5	5	5	5	5	60g/ha
392(R)	5	5	5	5	5	5	60g/ha
393	5	5	5	5	5	5	60g/ha
393(R)	5	5	5	5	5	5	60g/ha
394	5	5	5	5	5	5	60g/ha
394(R)	5	5	5	5	5	5	60g/ha
395	5	5	5	5	5	5	60g/ha
395(R)	5	5	5	5	5	5	60g/ha
396	5	5	5	5	5	5	60g/ha
396(R)	5	5	5	5	5	5	60g/ha
398	5	5	5	5	5	5	15g/ha
398(R)	5	5	5	5	5	5	15g/ha
399	5	5	5	5	5	5	15g/ha
399(R)	5	5	5	5	5	5	15g/ha
400	5	5	5	5	4	5	15g/ha
400(R)	5	5	5	5	5	5	15g/ha
406	5	5	5	5	4	5	15g/ha
406(R)	5	5	5	5	5	5	15g/ha
409	5	5	5	5	5	5	30g/ha
409(R)	5	5	5	5	5	5	30g/ha
416	5	5	5	5	4	5	15g/ha
416(R)	5	5	5	5	5	5	15g/ha
419	5	5	5	5	5	5	15g/ha
419(R)	5	5	5	5	5	5	15g/ha
421	5	5	5	5	5	5	15g/ha
421(R)	5	5	5	5	5	5	15g/ha
424	5	5	5	5	5	5	30g/ha
424(R)	5	5	5	5	5	5	30g/ha
426	5	5	5	5	5	5	250g/ha
426(R)	5	5	5	5	5	5	250g/ha
431	5	5	5	5	5	5	15g/ha
431(R)	5	5	5	5	5	5	15g/ha
432	5	5	5	5	5	5	15g/ha
432(R)	5	5	5	5	5	5	15g/ha
433	5	5	5	5	5	5	15g/ha
434	5	5	5	5	5	5	30g/ha
438	5	5	5	5	5	5	30g/ha
438(R)	5	5	5	5	5	5	30g/ha
439	5	5	5	5	5	5	30g/ha
439(R)	5	5	5	5	5	5	30g/ha
442	5	5	5	5	5	5	15g/ha
442(R)	5	5	5	5	5	5	15g/ha
443	5	5	5	5	5	5	15g/ha
443(R)	5	5	5	5	5	5	15g/ha
444	5	5	5	5	5	5	15g/ha
444(R)	5	5	5	5	5	5	15g/ha
445	5	5	5	5	5	5	15g/ha
445(R)	5	5	5	5	5	5	15g/ha
446	5	5	5	5	5	5	15g/ha
446(R)	5	5	5	5	5	5	15g/ha
447	5	5	5	5	5	5	15g/ha
447(R)	5	5	5	5	5	5	15g/ha
448	5	5	5	5	5	5	15g/ha
448(R)	5	5	5	5	5	5	15g/ha
449	5	5	5	5	5	5	15g/ha
449(R)	5	5	5	5	5	5	15g/ha
450	5	5	5	5	5	5	15g/ha
450(R)	5	5	5	5	5	5	15g/ha
451	N	N	N	N	N	5	15g/ha
451(R)	N	N	N	N	N	5	15g/ha
452	N	N	N	N	N	5	15g/ha
452(R)	N	N	N	N	N	5	15g/ha
453	5	5	5	5	5	5	30g/ha
453(R)	5	5	5	5	5	5	30g/ha
454	5	5	5	5	5	5	60g/ha
454(R)	5	5	5	5	5	5	60g/ha
455	5	5	5	5	5	5	15g/ha
455(R)	5	5	5	5	5	5	15g/ha
456	5	5	5	5	5	5	30g/ha
456(R)	5	5	5	5	5	5	30g/ha
462	5	5	5	5	5	5	15g/ha
462(R)	5	5	5	5	5	5	15g/ha
463	5	5	5	5	5	5	15g/ha
463(R)	5	5	5	5	5	5	15g/ha
469	5	5	5	5	5	5	15g/ha
471	N	N	N	N	N	5	15g/ha
471(R)	N	N	N	N	N	5	15g/ha
473	5	5	5	5	5	5	30g/ha
473(R)	5	5	5	5	5	5	30g/ha
475	N	N	N	N	N	5	15g/ha
475(R)	N	N	N	N	N	5	15g/ha
476	N	N	N	N	N	5	15g/ha
476(R)	N	N	N	N	N	5	15g/ha
477	N	N	N	N	N	5	15g/ha
477(R)	N	N	N	N	N	5	15g/ha
478	N	N	N	N	N	5	60g/ha
478(R)	N	N	N	N	N	5	60g/ha
479	N	N	N	N	N	5	15g/ha
480	N	N	N	N	N	5	15g/ha
481	N	N	N	N	N	5	15g/ha
481(R)	N	N	N	N	N	5	15g/ha
485	5	5	5	5	5	5	15g/ha
486	5	5	5	5	5	5	15g/ha
487	5	5	5	5	5	5	15g/ha
488	5	5	5	5	5	5	15g/ha
489	5	5	5	5	5	5	15g/ha
490	5	5	5	5	5	5	15g/ha
491	5	5	5	5	5	5	15g/ha
491(R)	5	5	5	5	5	5	15g/ha
493	5	5	5	5	5	5	15g/ha
494	5	5	5	5	5	5	15g/ha
495	5	5	5	5	5	5	15g/ha
495(R)	5	5	5	5	5	5	15g/ha
496	5	5	5	5	5	5	15g/ha
497	5	5	5	5	5	5	15g/ha
498	5	5	5	5	5	5	15g/ha
498(R)	5	5	5	5	5	5	15g/ha
499	5	5	5	5	5	5	15g/ha
499(R)	5	5	5	5	5	5	15g/ha
500	5	5	5	5	5	5	15g/ha
500(R)	5	5	5	5	5	5	15g/ha
501	5	5	5	5	5	5	15g/ha
501(R)	5	5	5	5	5	5	15g/ha
502	5	5	5	5	5	5	15g/ha
502(R)	5	5	5	5	5	5	15g/ha
503	5	5	5	5	5	5	15g/ha
503(R)	5	5	5	5	5	5	15g/ha
504	5	5	5	5	5	5	15g/ha
504(R)	5	5	5	5	5	5	15g/ha
511	5	5	5	5	5	5	15g/ha
692	5	5	5	5	5	5	15g/ha
730	5	5	5	5	5	5	15g/ha
730(R)	5	5	5	5	5	5	15g/ha
881	5	5	5	5	5	5	30g/ha
885	5	5	5	5	5	5	30g/ha
919	5	5	5	5	5	5	30g/ha
919(R)	5	5	5	5	5	5	30g/ha
Control compound A	1	0	1	1	0	3	15g/ha
Control compound B	2	2	2	1	1	3	15g/ha
Control compound C	2	2	2	1	1	2	15g/ha
Control compound D	3	4	3	3	2	N	15g/ha
Control compound E	3	4	4	3	3	N	15g/ha
Control compound F	1	0	1	1	0	2	60g/ha

Note: N represents untested;

Control compound A:

Control compound B:

Control compound C:

Control compound D:

Control compound E:

Control compound F:

Table 3. Results of R configuration, S configuration and racemate on weeding effect in post-emergence stage

Compound NO.	Amaranthus retroflexus	Echinochloa crusgalli	Eleusine indica	Dose
1(R)	5	4	5	7.5g/ha
1	3	3	3	7.5g/ha
1(S)	1	1	1	7.5g/ha
194(R)	5	5	5	7.5g/ha
194	5	4	4	7.5g/ha
194(S)	2	1	1	7.5g/ha
Control compound D	2	1	2	7.5g/ha

Experiment on weed effect in pre-emergence stage:

[0079] The aforementioned seeds of monocotyledonous and dicotyledonous weeds and main crops were put into a plastic pot loaded with soil and covered with 0.5-2cm soil. The test compounds of the present invention was dissolved with acetone, then added with tween 80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 500,250,125,60,30,15,7.5 g a.i./ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc.. And many compounds had good selectivity for corn, cotton, wheat, rice, soybean, and peanut etc.. In addition, evaluate the weed control effect with the above activity standard level. Many compounds show excellent activity and selectivity, which are shown in Table 4.

Table 4. Results on weeding effect in pre -emergence stage

Compou nd NO.	Veron ica didy ma Tenor e	Descu rainia sophia	Capsel la bursa-pastori s	Abutil on theoph rasti	Amara nthus retrofl exus	Setari a viridis	Corn	Cotton	So ybe ans	Pe an ut	Dose
1(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
2(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
194(R)	5	5	5	5	5	5	0	0	0	0	15g/ha
194(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
194(R)	5	5	5	5	5	5	0	0	0	0	60g/ha
196(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
198(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
199(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
208(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
212(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
216(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
218(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
239(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
246(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
248(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
249(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
253(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
258(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
264(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
283(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
301(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
315(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
333(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
349(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
398(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
421(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
431(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
432(R)	5	5	5	5	5	5	0	0	0	0	30g/ha
433	5	5	5	5	5	5	0	0	0	0	30g/ha
434	5	5	5	5	5	5	0	0	0	0	30g/ha

[0080] It is indicated from the experiment of main weeds in wheat and rice fields that the compound of the present invention generally have good weed control efficacy. Above all, it is noted that the compound of the invention have extremely high activity to broad-leaved weeds and cyperaceae weeds, which are resistant to ALS inhibitor, like Sagittaria trifolia, Scirpus juncoides, Cyperus difformis, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine L., and Cyperus rotundus L., etc. , and have excellent commercial value.

Transplanted rice safety evaluation and weed control effect evaluation in rice field:

[0081] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Monochoria vaginalis, and Leptochloa chinensis were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1cm of water storage. The tuber of Sagittaria trifolia was planted in the next day or 2 days later. It was kept at 3-4cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Monochoria vaginalis, and Leptochloa chinensis reached 0.5 leaf stage and Sagittaria trifolia reached the time point of primary leaf stage.

[0082] In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4cm depth. The 5 leaf stage rice (japonica rice) was transplanted at 3cm of transplanting depth the next day. The compound of the present invention was treated by the same way after 5 days of transplantation.

[0083] The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Monochoria vaginalis, Leptochloa chinensis and Sagittaria trifolia 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with the above activity standard level. Many compounds show excellent activity and selectivity.

Table 5. Evaluation effect of some compounds

Compound NO.	Leptochloa chinensis	Scirpus juncoides	Monochoria vaginalis	Rice	Dose
194(R)	5	5	5	0	30 g/ha
196(R)	5	5	5	0	30 g/ha
212(R)	5	5	5	0	30 g/ha
218(R)	5	5	5	0	30 g/ha
421(R)	5	5	5	0	30 g/ha
434	5	5	5	0	30 g/ha
Pyrazosulfuron -ethyl	2	1	2	1	30 g/ha

Note: The seeds of Echinochloa crusgalli, Scirpus juncoides, Monochoria vaginalis and Bidens tripartita L., Sagittaria trifolia were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyl.

Composition activity test:

[0084] The active ingredient B shuangzuocaotong, huanbifucaotong, benzuofucaotong, and sanzuohuangcaotong was produced by our company, the preparation methods of

are as follows, and the others were purchased from reagent companies. The technical materials were all dissolved in acetone and diluted with an aqueous solution containing 0.1% emulsifier Tween-80. The dilution is performed as required.

(1) Synthesis of Compound

(1.1) Cpd 1(3 g, 16 mmol, 1.0 eq), NaOH (0.72 g, 18 mmol, 1.1 eq) were added sequentially into 30 ml of DMF, and then Cpd 2 (1.28 g, 16.8 mmol, 1.05 eq) was added dropwise at 0 °C, and the reaction solution was stirred at 0 °C for 1 hour. When LCMS test showed that the reaction of raw materials was basically completed, there was one major new peak. The reaction solution was poured into 30 ml of water, and the mixture was separated, and the aqueous phase was extracted once with 50 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, evaporated to dryness under reduced pressure and separated by column chromatography to obtain Cpd 3 (3.6 g, 91% yield) (colorless oil).

(1.2) Cpd 3(3.1 g, 13 mmol, 1.0 eq) was added to 30 ml of THF, then n-BuLi (6.42 ml, 2.5 M, 16 mmol, 1.2 eq) was slowly added at -78 °C, then the reaction solution was stirred at -78 °C for 0.5 hour, and slowly fed with CO₂ for 10 minutes, then the reaction solution was slowly warmed to room temperature. The product was detected by LCMS. 20 ml of water was poured into the reaction solution, the mixture was separated, the aqueous phase was extracted once with 30 ml of ethyl acetate, and the resultant aqueous phase was gradually adjusted to pH = 4-5 with concentrated hydrochloric acid, filtered and dried to give Cpd 4(3.2 g, 87% yield) (white solid).

(1.3) Cpd 4(3.1 g, 11 mmol, 1.0 eq), Cpd 5 (1.66 g, 16.8 mmol, 1.5 eq), DMAP (0.13 g, 1.1 mmol, 0.1 eq) were sequentially added to 30 ml of pyridine. Then, SOCl₂ (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0 °C, and the reaction solution was stirred at room temperature for 3 hours. The product was detected by LCMS. Pyridine was removed by concentration, then 30 ml of water was poured into the reaction solution, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, and evaporated to dryness under reduced pressure and separated by column chromatography to to obtain Cpd 6(2.5 g, 63% yield) (white solid).

(1.4) Cpd 6(1 g, 2.8 mmol, 1.0 eq) and m-CPBA (0.54 g, 3.1 mmol, 1.1 eq) were added sequentially in 10 mL of dichloromethane. The reaction solution was then stirred at room temperature for 1 hour. The product was detected by LCMS, and the reaction of raw materials was basically completed. The reaction solution was poured into 10 ml of water, the reaction was quenched with sodium hydrogen sulfite, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of dichloromethane, and the resultant organic phase was washed once with saturated saline solution (30 ml), dried, and evaporated to dryness under reduced pressure, and separated by column chromatography to give Cpd 7(0.85 g, 82% yield) (greyish white solid).
¹H NMR (500 MHz, DMSO-d₆) 12.57 (s, 1H), 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 3.57-3.47 (m, 2H), 2.48 (s, 3H), 1.70-1.52 (m, 2H), 1.08-0.93 (m, 3H).

(1.5) Cpd 7 (0.5 g, 98% purity) was passed through chiral HPLC (Column: CHIRALPAK IG; Column Size: 3 cm × 25 cm, 5 um; Injection: 3.0 ml; Mobile phase: Hex(0.2% FA) : IPA=50:50; Flow rate: 28ml/min; Wavelength: UV 254nm; Temperature: 25 °C; Sample solution: 70mg/ml in EtOH/DCM; Run time= 60 mins) for separation, and then concentrated to obtain Cpd B1 (R-configuration)(0.16 g, Rt=10.51min, 100% ee, purity 98%) in white solids, which were confirmed by single crystal diffraction.

(2) Synthesis of Compound

[0085] (2.1) Cpd a (0.5g, 2.13mmol), Cpd b (313mg, 2.55mmol), a catalytic amount of TBAB (10mg), and DMF (10mL) were added to a round-bottom flask, and stirred at room temperature 15 °C for 24 hr. When there was a small amount of raw materials remained according to LC-MS detection, a further treatment was made. The reaction solution was poured into 50mL of water, and extracted with methyl tert-butyl ether twice (50mL × 2). The organic phase was dried, concentrated, and separated by column chromatography, to obtain Cpd c (300mg, yield 50%), as a white solid.

[0086] (2.2) Cpd c (0.3g, 1.06mmol), methanol (20mL) were added to a 100 mL single-port flask, lithium hydroxide (44.5mg, 1.06mmol) was dissolved in 2 mL of water, and slowly added dropwise to the single-port flask at room temperature, followed by stirring at room temperature for 12 hr. After completed reaction of the raw materials according to LC-MS detection, the reaction solution was adjusted with 0.5M dilute HCl to pH = 5-6, concentrated, and then extracted with water and ethyl acetate. The organic phase was dried, and concentrated to obtain Cpd d (200mg, yield 70%) as a white solid.

[0087] (2.3) Cpd d (200mg, 0.74mmol), Cpd e (75mg, 0.74mmol), DCC (152mg, 0.74mmol), and anhydrous DCM (20mL) were added to a 100 mL round-bottom flask, and reacted at room temperature for 12 hr. After completed reaction of the raw materials according to LC-MS detection, the reaction solution was concentrated, and separated by column chromatography to obtain the Cpd B2 (200mg, yield 77%), as a white solid.

[0088] ¹H NMR (500 MHz, Chloroform-d) δ 5.28 (q, J = 7.0 Hz, 1H), 5.15 (s, 2H), 4.27 - 4.07 (m, 3H), 3.91 - 3.73 (m, 2H), 2.04 - 1.82 (m, 3H), 1.66 (d, J = 7.0 Hz, 3H), 1.59-1.54 (m, 1H).

(A)Post-emergence treatment by performing foliage spray:

[0089] Weeds were cultivated by a pot culture method. A 180 ×140 mm plastic nutritional bowl contained 4/5 topsoil from the field was placed in an enamel pan, wherein the soil had been air-dried and screened and had an initial moisture content of 20%. Full and uniform weed seeds were selected, soaked in warm water at 25°C for 6 hours, and germinated in a 28°C biochemical incubator (darkness). The weed seeds that had just germinated were evenly placed on the surface of the soil and then covered with 0.5-1 cm soil according to the sizes of seeds.

[0090] The culture was carried out in a controllable sunlight greenhouse at 20 to 30°C, in natural light, and relative humidity of 57% to 72%. The soil was loam with an organic matter content of 1.63%, a pH value of 7.1, an alkali-hydrolyzable nitrogen of 84.3 mg/kg, a rapidly available phosphorus of 38.5 mg/kg, and a rapidly available potassium 82.1 mg/kg.

[0091] 3 pots with 20 weed seeds per pot were treated in one treatment with 4 replications per treatment.

[0092] The agents were used for only once in the experiment. In the stage of weeds with 1.5-2 leaves, the weeds were thinned out to maintain 10 weeds per pot and 30 weeds for each treatment, then continued to be cultured to Conyza Canadensis 10cm in height, other weeds 3-4 leaves stage and treated.

[0093] The well-cultured weeds were evenly placed on a platform with an area of 0.5m², and a solution of agents was sprayed on the stems and leaves thereof by the 3WP-2000-type walking spray tower at a dosage of 450kg/ha and at a spray pressure of 0.3MPa. After all the solution was sprayed, the valve was closed. After 30 seconds, the door of the spray tower was opened, and the nutritional bowl was taken out. Then the valve was opened, and the spray tube was cleaned by spraying 50 ml of water. After the treatment, the weeds were routinely cultured in a greenhouse.

(B)Soil sealing treatment:

[0094] Weeds are cultivated in a controllable sunlight greenhouse at 20 to 30°C, in natural light, and relative humidity of 57% to 72%. The soil was loam with an organic matter content of 1.63%, a pH value of 7.1, an alkali-hydrolyzable nitrogen of 84.3 mg/kg, a rapidly available phosphorus of 38.5 mg/kg, and a rapidly available potassium 82.1 mg/kg. The test soil was placed quantitatively to 3/4 of the pots and then watered from the bottom of the pots to completely wet the soil to saturation. The test weed seeds were germinated, and uniformly and quantitatively sowed on the surface, then covered with 0.5-2 cm soil according to the seed size, and ready-for use 72 hours after sowing.

[0095] 3 pots with 30 weed seeds per pot were treated in one treatment with 4 replications per treatment.

[0096] The well-sowed weeds were evenly placed on a platform with an area of 0.5m², and a solution of agents was sprayed on the soil thereof by the 3WP-2000-type walking spray tower at a dosage of 450kg/ha and at a spray pressure of 0.3MPa. After all the solution was sprayed, the valve was closed. After 30 seconds, the door of the spray tower was opened, and the nutritional bowl was taken out. Then the valve was opened, and the spray tube was cleaned by spraying 50 ml of water.

(C)Data investigation and statistical analysis:

[0097] A method for investigating absolute number was employed, wherein whole seedlings of survival weeds were cut off with a blade along the soil surface, and the fresh weight of the weeds was weighed with an analytical balance. For dead weeds, the fresh weight thereof was zero.

[0098] The investigation was performed after 21 days of the treatment for only once.

[0099] Theoretical fresh weight inhibition rate of a combination of two active ingredients in each group was calculated by the Gowing method (E0=X+Y-X^∗Y/100), and then compared with an actually measured inhibition rate (E), thereby effect of the combination (hereafter referred to as combined effect) on weeds was evaluated: the value of E-E0, which was greater than 10%, corresponded to a synergistic effect, the value of E-E0, which was less than -10%, corresponded to an antagonistic effect, and the value of E-E0, which was from -10% to 10%, corresponded to an additional effect. An optimum ratio of the two active ingredients was determined by the actual control effect, characteristics of herbicides, and balance of a corresponding formula. Wherein, in the formula, X represented the fresh weight inhibition rate of the active ingredient A in a dosage of P, and Y represented the fresh weight inhibition rate of the active ingredient B in a dosage of Q. The statistical results were shown in the table 6.

Table 6. Actual control effect and combined effect of a combination of A on weeds

Components	Weed	Foliage /Soil F/ S	Dose g a.i./ha	Ratio	Contro 1 effect (%) of A applied alone (A)	Contro 1 effect (%) of B applied alone (B)	Actual control effect of A+B (%) E(A+B)	Theoretica 1 control effect of A+B(%) E0(A+B)	E(A+B) -E0(A+ B)
A +topramezo ne	Echino chloa caudat a Roshev	F	1.5+7.5	1:5	65.9	38.5	93.5	79.0	14.5
A +isoxaflutol e	Echino chloa caudat a Roshev	F	1.5+15	1:10	65.9	41.3	91.9	80.0	11.9
A +tembotrio ne	Echino chloa caudat a Roshev	F	1.5+15	1:10	65.9	31.7	88.3	76.7	11.6
A +tefuryltrio ne	Echino chloa caudat a Roshev	F	1.5+30	1:20	65.9	21.5	86.6	73.2	13.4
A +shuangzuo caotong	Echino chloa caudat a Roshev	F	1.5+15	1:10	65.9	35.9	94.5	78.1	16.4
A +huanbifuc aotong	Echino chloa caudat a Roshev	F	1.5+60	1:40	65.9	27.4	87.4	75.2	12.2
A +sanzuohua ngcaotong	Echino chloa caudat a Roshev	F	1.5+30	1:20	65.9	56.7	98.4	85.2	13.2
A +benzuofuc aotong	Echino chloa caudat a Roshev	F	1.5+15	1:10	65.9	25.2	89.9	74.5	15.4
A+CpdB1	Echino chloa caudat a Roshev	F	1.5+7.5	1:5	65.9	47.8	96.2	82.2	14.0
A +glyphosat e	Cyperu s rotund us	F	7.5+300	1:40	52.4	19.4	82.4	61.6	20.8
A +glyphosat e	Conyza Canad ensis	F	45+450	1:10	75.6	51.2	100.0	88.1	11.9
A +glufosinat e ammonium	Cyperu s serotin us	F	15+300	1:20	47.3	23.1	90.2	59.5	30.7
A +glufosinat e ammonium	Conyza Canad ensis	F	45+300	3:20	75.6	57.8	100.0	89.7	10.3
A +glufosinat e-P-ammoniu m	Cyperu s serotin us	F	15+150	1:10	47.3	21.4	85.3	58.6	26.7
A +paraquat dichloride	Cyperu s difform is	F	15+150	1:10	42.2	35.7	87.4	62.8	24.6
A +paraquat dichloride	Conyza Canad ensis	F	45+225	1:5	75.6	48.4	100.0	87.4	12.6
A+diquat dibromide monohydrate	Cyperu s difform is	F	15+300	1:20	42.2	18.4	79.2	52.8	26.4
A+diquat dibromide monohydrate	Conyza Canad ensis	F	45+300	3:20	75.6	37.8	100.0	84.8	15.2
A+flurtamon e	Capsel la bursa-pastori s	F	0.75+75	1:100	48.3	56.7	95.4	77.6	17.8
A +difl ufenic an	Capsel la bursa-pastori s	F	0.75+75	1:100	48.3	33.1	86.7	65.4	21.3
A +picolinafe n	Capsel la bursa-pastori s	F	0.75+45	1:60	48.3	44.4	91.5	71.3	20.2
A+clomazon e	Eleusin e indica	F	3+150	1:50	47.8	46.5	95.1	72.1	23.0
A +bixlozone	Eleusin e indica	F	3+180	1:60	47.8	36.7	88.8	67.0	21.8
A +tribenuron -methyl	Malac hium aquatic um	F	7.5+3	5:2	62.8	27.9	90.1	73.2	16.9
A +thifensulf uron methyl	Malac hium aquatic um	F	7.5+4.5	5:3	62.8	30.8	87.2	74.3	12.9
A +pyrazosulf uron-ethyl	Malac hium aquatic um	F	7.5+7.5	1:1	62.8	35.7	89.5	76.1	13.4
A +thiencarba zone-methyl	Malac hium aquatic um	F	7.5+3	5:2	62.8	41.1	93.3	78.1	15.2
A+halosulfur on methyl	Malac hium aquatic um	F	7.5+9	5:6	62.8	36.4	94.7	76.3	18.4
A +rimsulfuro n	Malac hium aquatic um	F	7.5+1.5	5:1	62.8	26.2	92.4	72.5	19.9
A +nicosulfur on	Malac hium aquatic um	F	7.5+3	5:2	62.8	31.4	88.5	74.5	14.0
A +imazamox	Malac hium aquatic um	F	7.5+15	1:2	62.8	27.2	91.2	72.9	18.3
A +clethodim	Eriochl oa villosa	F	0.75+30	1:40	42.9	35.5	89.5	63.2	26.3
A +sethoxydi m	Eriochl oa villosa	F	0.75+45	1:60	42.9	36.7	92.3	63.9	28.4
A +quizalofop -P-methyl	Eriochl oa villosa	F	0.75+15	1:20	42.9	41.7	87.3	66.7	20.6
A +oxyfluorfe n	Lithosp ermum arvens e	F	3+60	1:20	63.5	31.5	91.4	75.0	16.4
A +oxadiazon	Lithosp ermum arvens e	F	3+90	1:30	63.5	24.3	92.1	72.4	19.7
A +oxadiargyl	Lithosp ermum arvens e	F	3+30	1:10	63.5	38.7	89.8	77.6	12.2
A +sulfentraz one	Lithosp ermum arvens e	F	3+90	1:30	63.5	26.5	94.1	73.2	20.9
A +pyraclonil	Lithosp ermum arvens e	F	3+75	1:25	63.5	37.9	90.5	77.3	13.2
A+flumioxaz in	Lithosp ermum arvens e	F	3+7.5	2:5	63.5	29.4	92.4	74.2	18.2
A +saflufenac il	Lithosp ermum arvens e	F	3+0.75	4:1	63.5	39.7	98.4	78.0	20.4
A +carfentraz one-ethyl	Lithosp ermum arvens e	F	3+4.5	2:3	63.5	27.2	89.3	73.4	15.9
A +trifludimo xazin	Lithosp ermum arvens e	F	3+4.5	2:3	63.5	31.8	94.8	75.1	19.7
A+metribuzi n	Eclipta prostra te	F	0.75+15	1:20	59.2	36.3	89.3	74.0	15.3
A+terbuthyla zinc	Eclipta prostra te	F	0.75+150	1:200	59.2	31.7	94.1	72.1	22.0
A +amicarbaz one	Eclipta prostra te	F	0.75+60	1:80	59.2	43.7	90.7	77.0	13.7
A+chlorotolu ron	Eclipta prostra te	F	0.75+225	1:300	59.2	24.5	86.2	69.2	17.0
A +isoproturo n	Eclipta prostra te	F	0.75+225	1:300	59.2	33.9	92.5	73.0	19.5
A +bromacil	Eclipta prostra te	F	0.75+450	1:600	59.2	28.4	83.9	70.8	13.1
A +propanil	Eclipta prostra te	F	0.75+300	1:400	59.2	21.7	93.8	68.1	25.7
A +desmedip ham	Eclipta prostra te	F	0.75+300	1:400	59.2	16.2	90.5	65.8	24.7
A +phenmedi pham	Eclipta prostra te	F	0.75+300	1:400	59.2	20.8	86.2	67.7	18.5
A +bentazone	Eclipta prostra te	F	0.75+150	1:200	59.2	30.2	88.4	71.5	16.9
A +bromoxyn il	Eclipta prostra te	F	0.75+60	1:80	59.2	41.2	92.6	76.0	16.6
A +butralin	Leptoc hloa chinen sis	S	3+180	1:60	33.2	47.4	92.3	64.9	27.4
A +pendimeth alin	Leptoc hloa chinen sis	S	3+150	1:50	33.2	43.2	85.8	62.1	23.7
A +butachlor	Descur ainia sophia	S	3+225	1:75	40.2	42.2	92.3	65.4	26.9
A +pretilachl o r	Descur ainia sophia	S	3+180	1:60	40.2	51.2	95.7	70.8	24.9
A+mefenacet	Descur ainia sophia	S	3+150	1:50	40.2	46.4	89.6	67.9	21.7
A +s-metolac hlor	Descur ainia sophia	S	3+150	1:50	40.2	31.3	94.3	58.9	35.4
A+flufenacet	Descur ainia sophia	S	3+150	1:50	40.2	45.6	96.3	67.5	28.8
A +pyroxasulf one	Descur ainia sophia	S	3+60	1:20	40.2	57.6	98.2	74.6	23.6
A +anilofos	Descur ainia sophia	S	3+75	1:25	40.2	38.3	97.3	63.1	34.2
A +prosulfoca rb	Echino chloa crusgal li	S	15+600	1:40	51.7	32.6	86.9	67.4	19.5
A+ Cpd B2	Veronica didyma Tenore	F	0.75+90	1:120	57.3	42.1	92.6	75.3	17.3
A+fluroxypyr	Veronic didyma Tenore	F	0.75+60	1:80	57.3	39.3	90.3	74.1	16.2
A +florpyraux ifen benzyl	Veronic a didyma Tenore	F	0.75+15	1:20	57.3	50.3	91.5	78.8	12.7
A +halauxifen -methyl	Veronic a didyma Tenore	F	0.75+3	1:4	57.3	35.6	87.6	72.5	15.1
A+triclopyr	Veronic didyma Tenore	F	0.75+90	1:120	57.3	34.2	91.5	71.9	19.6
A+clopyralid	Veronic didyma Tenore	F	0.75+45	1:60	57.3	28.9	83.3	69.6	13.7
A +picloram	Veronic didyma Tenore	F	0.75+300	1:400	57.3	43.6	88.7	75.9	12.8
A +aminopyra lid	Veronic a didyma Tenore	F	0.75+30	1:40	57.3	32.2	90.2	71.0	19.2
A+dicamba	Veronic didyma Tenore	F	0.75+150	1:200	57.3	29.7	87.3	70.0	17.3
A+2-methyl-4-chlorophen oxyacetic acid	Veronic a didyma Tenore	F	0.75+150	1:200	57.3	39.3	90.9	74.1	16.8
A+2,4-dichlo rophenoxy acetic acid	Veronic a didyma Tenore	F	0.75+150	1:200	57.3	32.6	85.2	71.2	14.0
A +triaziflam	Amara nthus retrofle xus	S	3+30	1:10	37.3	42.1	91.3	63.7	27.6
A +indaziflam	Amara nthus retrofle xus	S	3+15	1:5	37.3	49.3	93.3	68.2	25.1
A +cinmethyli n	Lolium multifl orum Lamk.	S	30+300	1:10	48.6	33.7	87.3	65.9	21.4

Note: The compound number represented by A is 194 (R).

[0100] In addition, the present invention also provides other specific combinations of component A and component B, to further illustrate the composition of the present invention. The compounds in the column "Component A (Compound No.)" are identified in Table 1. The second column of Table B1 lists specific compounds (for example "topramezone" in the first row) for component B. The remaining rows of Table B1 are similarly constructed.

Table B1. List of ingredients of the composition

Component A (Compound NO.)	Component B
1	topramezone
1	isoxaflutole
1	tembotrione
1	tefuryltrione
1	shuangzuocaotong
1	huanbifucaotong
1	sanzuohuangcaotong
1	benzuofucaotong
1
1	glyphosate
1	glufosinate ammonium
1	glufosinate- P-ammonium
1	paraquat dichloride
1	diquat dibromide monohydrate
1	flurtamone
1	diflufenican
1	picolinafen
1	clomazone
1	bixlozone
1	tribenuron-methyl
1	thifensulfuron methyl
1	pyrazosulfuron -ethyl
1	thiencarbazone-methyl
1	halosulfuron methyl
1	rimsulfuron
1	nicosulfuron
1	imazamox
1	clethodim
1	sethoxydim
1	quizalofop-P-methyl
1	oxyfluorfen
1	oxadiazon
1	oxadiargyl
1	sulfentrazone
1	pyraclonil
1	flumioxazin
1	saflufenacil
1	carfentrazone-ethyl
1	trifludimoxazin
1	metribuzin
1	terbuthylazine
1	amicarbazone
1	chlorotoluron
1	isoproturon
1	bromacil
1	propanil
1	desmedipham
1	phenmedipham
1	bentazone
1	bromoxynil
1	butralin
1	pendimethalin
1	butachlor
1	pretilachlor
1	mefenacet
1	s-metolachlor
1	flufenacet
1	pyroxasulfone
1	anilofos
1	pro sulfoc arb
1
1	fluroxypyr
1	florpyrauxifen benzyl
1	halauxifen-methyl
1	triclopyr
1	clopyralid
1	picloram
1	aminopyralid
1	dicamba
1	2-methyl-4-chlorophenoxyacetic acid
1	2,4-dichlorophenoxy acetic acid
1	triaziflam
1	indaziflam
1	cinmethylin

[0101] Table B2 is constructed in the same way as that of Table B1 above, except for replacing the entries in the column "Component A (Compound No.)" with the corresponding entries in the column "Component A (Compound No.)" shown below. Therefore, for example, in Table B2, the entries in the column "Component A (Compound No.)" are all expressed as "2" (that is, Compound 2 identified in Table 1), and a mixture of Compound 2 and "topramezone" is specifically listed in the first row under the heading of Table B2. Tables B3 to B552 are similarly constructed.

Table	"Component A (Compound NO.)" column entry	Table	" Component A (Compound NO.)" column , entry	Table	" Component A (Compound NO.)" column entry	Table	"Component A (Compound NO.)" column entry
B2	2	B3	3	B4	4	B5	5
B6	6	B7	7	B8	8	B9	9
B10	10	B11	11	B12	12	B13	13
B14	14	B15	15	B16	16	B17	17
B18	18	B19	19	B20	20	B21	21
B22	22	B23	23	B24	24	B25	25
B26	26	B27	27	B28	28	B29	29
B30	30	B31	31	B32	32	B33	33
B34	34	B35	35	B36	36	B37	37
B38	38	B39	39	B40	40	B41	41
B42	42	B43	43	B44	44	B45	45
B46	46	B47	47	B48	48	B49	49
B50	50	B51	51	B52	52	B53	53
B54	54	B55	55	B56	56	B57	57
B58	58	B59	59	B60	60	B61	61
B62	62	B63	63	B64	64	B65	65
B66	66	B67	67	B68	68	B69	69
B70	70	B71	71	B72	72	B73	73
B74	74	B75	75	B76	76	B77	77
B78	78	B79	79	B80	80	B81	81
B82	82	B83	83	B84	84	B85	85
B86	86	B87	87	B88	88	B89	89
B90	90	B91	91	B92	92	B93	93
B94	94	B95	95	B96	96	B97	97
B98	98	B99	99	B100	100	B101	101
B102	102	B103	103	B104	104	B105	105
B106	106	B107	107	B108	108	B109	109
B110	110	B111	111	B112	112	B113	113
B114	114	B115	115	B116	116	B117	117
B118	118	B119	119	B120	120	B121	121
B122	122	B123	123	B124	124	B125	125
B126	126	B127	127	B128	128	B129	129
B130	130	B131	131	B132	132	B133	133
B134	134	B135	135	B136	136	B137	137
B138	138	B139	139	B140	140	B141	141
B142	142	B143	143	B144	144	B145	145
B146	146	B147	147	B148	148	B149	149
B150	150	B151	151	B152	152	B153	153
B154	154	B155	155	B156	156	B157	157
B158	158	B159	159	B160	160	B161	161
B162	162	B163	163	B164	164	B165	165
B166	166	B167	167	B168	168	B169	169
B170	170	B171	171	B172	172	B173	173
B174	174	B175	175	B176	176	B177	177
B178	178	B179	179	B180	180	B181	181
B182	182	B183	183	B184	184	B185	185
B186	186	B187	187	B188	188	B189	189
B190	190	B191	191	B192	192	B193	193
B194	194	B195	195	B196	196	B197	197
B198	198	B199	199	B200	200	B201	201
B202	202	B203	203	B204	204	B205	205
B206	206	B207	207	B208	208	B209	209
B210	210	B211	211	B212	212	B213	213
B214	214	B215	215	B216	216	B217	217
B218	218	B219	219	B220	220	B221	221
B222	222	B223	223	B224	224	B225	225
B226	226	B227	227	B228	228	B229	229
B230	230	B231	231	B232	232	B233	233
B234	234	B235	235	B236	236	B237	237
B238	238	B239	239	B240	240	B241	241
B242	242	B243	243	B244	244	B245	245
B246	246	B247	247	B248	248	B249	249
B250	250	B251	251	B252	252	B253	253
B254	254	B255	255	B256	256	B257	257
B258	258	B259	259	B260	260	B261	261
B262	262	B263	263	B264	264	B265	265
B266	266	B267	267	B268	268	B269	269
B270	270	B271	271	B272	272	B273	273
B274	274	B275	275	B276	276	B277	277
B278	278	B279	279	B280	280	B281	281
B282	282	B283	283	B284	284	B285	285
B286	286	B287	287	B288	288	B289	289
B290	290	B291	291	B292	292	B293	293
B294	294	B295	295	B296	296	B297	297
B298	298	B299	299	B300	300	B301	301
B302	302	B303	303	B304	304	B305	305
B306	306	B307	307	B308	308	B309	309
B310	310	B311	311	B312	312	B313	313
B314	314	B315	315	B316	316	B317	317
B318	318	B319	319	B320	320	B321	321
B322	322	B323	323	B324	324	B325	325
B326	326	B327	327	B328	328	B329	329
B330	330	B331	331	B332	332	B333	333
B334	334	B335	335	B336	336	B337	337
B338	338	B339	339	B340	340	B341	341
B342	342	B343	343	B344	344	B345	345
B346	346	B347	347	B348	348	B349	349
B350	350	B351	351	B352	352	B353	353
B354	354	B355	355	B356	356	B357	357
B358	358	B359	359	B360	360	B361	361
B362	362	B363	363	B364	364	B365	365
B366	366	B367	367	B368	368	B369	369
B370	370	B371	371	B372	372	B373	373
B374	374	B375	375	B376	376	B377	377
B378	378	B379	379	B380	380	B381	381
B382	382	B383	383	B384	384	B385	385
B386	386	B387	387	B388	388	B389	389
B390	390	B391	391	B392	392	B393	393
B394	394	B395	395	B396	396	B397	397
B398	398	B399	399	B400	400	B401	401
B402	402	B403	403	B404	404	B405	405
B406	406	B407	407	B408	408	B409	409
B410	410	B411	411	B412	412	B413	413
B414	414	B415	415	B416	416	B417	417
B418	418	B419	419	B420	420	B421	421
B422	422	B423	423	B424	424	B425	425
B426	426	B427	427	B428	428	B429	429
B430	430	B431	431	B432	432	B433	433
B434	434	B435	435	B436	436	B437	437
B438	438	B439	439	B440	440	B441	441
B442	442	B443	443	B444	444	B445	445
B446	446	B447	447	B448	448	B449	449
B450	450	B451	451	B452	452	B453	453
B454	454	B455	455	B456	456	B457	457
B458	458	B459	459	B460	460	B461	461
B462	462	B463	463	B464	464	B465	465
B466	466	B467	467	B468	468	B469	469
B470	470	B471	471	B472	472	B473	473
B474	474	B475	475	B476	476	B477	477
B478	478	B479	479	B480	480	B481	481
B482	482	B483	483	B484	484	B485	485
B486	486	B487	487	B488	488	B489	489
B490	490	B491	491	B492	492	B493	493
B494	494	B495	495	B496	496	B497	497
B498	498	B499	499	B500	500	B501	501
B502	502	B503	503	B504	504	B505	505
B506	506	B507	507	B508	508	B509	509
B510	510	B511	511	B512	512	B513	513
B514	514	B515	515	B516	516	B517	517
B518	518	B519	519	B520	520	B521	521
B522	522	B523	523	B524	524	B525	525
B526	526	B527	527	B528	528	B529	529
B530	530	B531	531	B532	532	B533	533
B534	534	B535	535	B536	536	B537	537
B538	538	B539	539	B540	540	B541	541
B542	542	B543	543	B544	544	B545	545
B546	546	B547	547	B548	692	B549	730
B550	881	B551	885	B552	919

[0102] Table C1 is constructed in the same way as that of Table B1 above, except for replacing the entries in the column "Component A (Compound No.)" with the corresponding entries in the column "Component A (Compound No.)" shown below. Therefore, for example, in Table C1, the entries in the column "Component A (Compound No.)" are all expressed as "1(R)" (that is, the R configuration of Compound 1 identified in Table A), and a mixture of Compound 1(R) and "topramezone" is specifically listed in the first row under the heading of Table C1. Tables C2 to C535 are similarly constructed.

Table	"Component A (Compound NO.)" column entry	Table	"Component A (Compound NO.)" column entry	Table	"Component A (Compound NO.)" column entry	Table	"Component A (Compound NO.)" column entry
C2	2(R)	C3	3(R)	C4	4(R)	C5	5(R)
C6	6(R)	C7	7(R)	C8	8(R)	C9	9(R)
C10	10(R)	C11	11(R)	C12	12(R)	C13	13(R)
C14	14(R)	C15	15(R)	C16	16(R)	C17	17(R)
C18	18(R)	C19	19(R)	C20	20(R)	C21	21(R)
C22	22(R)	C23	23(R)	C24	24(R)	C25	25(R)
C26	26(R)	C27	27(R)	C28	28(R)	C29	29(R)
C30	30(R)	C31	31(R)	C32	32(R)	C33	33(R)
C34	34(R)	C35	35(R)	C36	36(R)	C37	37(R)
C38	38(R)	C39	39(R)	C40	40(R)	C41	41(R)
C42	42(R)	C43	43(R)	C44	44(R)	C45	45(R)
C46	46(R)	C47	47(R)	C48	48(R)	C49	49(R)
C50	50(R)	C51	51(R)	C52	52(R)	C53	53(R)
C54	54(R)	C55	55(R)	C56	56(R)	C57	57(R)
C58	58(R)	C59	59(R)	C60	60(R)	C61	61(R)
C62	62(R)	C63	63(R)	C64	64(R)	C65	65(R)
C66	66(R)	C67	67(R)	C68	68(R)	C69	69(R)
C70	70(R)	C71	71(R)	C72	72(R)	C73	73(R)
C74	74(R)	C75	75(R)	C76	76(R)	C77	77(R)
C78	78(R)	C79	79(R)	C80	80(R)	C81	81(R)
C82	82(R)	C83	83(R)	C84	84(R)	C85	85(R)
C86	86(R)	C87	87(R)	C88	88(R)	C89	89(R)
C90	90(R)	C91	91(R)	C92	92(R)	C93	93(R)
C94	94(R)	C95	95(R)	C96	96(R)	C97	97(R)
C98	98(R)	C99	99(R)	C100	100(R)	C101	101(R)
C102	102(R)	C103	103(R)	C104	104(R)	C105	105(R)
C106	106(R)	C107	107(R)	C108	108(R)	C109	109(R)
C110	110(R)	C111	111(R)	C112	112(R)	C113	113(R)
C114	114(R)	C115	115(R)	C116	116(R)	C117	117(R)
C118	118(R)	C119	119(R)	C120	120(R)	C121	121(R)
C122	122(R)	C123	123(R)	C124	124(R)	C125	125(R)
C126	126(R)	C127	127(R)	C128	128(R)	C129	129(R)
C130	130(R)	C131	131(R)	C132	132(R)	C133	133(R)
C134	134(R)	C135	135(R)	C136	136(R)	C137	137(R)
C138	138(R)	C139	139(R)	C140	140(R)	C141	141(R)
C142	142(R)	C143	143(R)	C144	144(R)	C145	145(R)
C146	146(R)	C147	147(R)	C148	148(R)	C149	149(R)
C150	150(R)	C151	151(R)	C152	152(R)	C153	153(R)
C154	154(R)	C155	155(R)	C156	156(R)	C157	157(R)
C158	158(R)	C159	159(R)	C160	160(R)	C161	161(R)
C162	162(R)	C163	163(R)	C164	164(R)	C165	165(R)
C166	166(R)	C167	167(R)	C168	168(R)	C169	169(R)
C170	170(R)	C171	171(R)	C172	172(R)	C173	173(R)
C174	174(R)	C175	175(R)	C176	176(R)	C177	177(R)
C178	178(R)	C179	179(R)	C180	180(R)	C181	181(R)
C182	182(R)	C183	183(R)	C184	184(R)	C185	185(R)
C186	186(R)	C187	187(R)	C188	188(R)	C189	193(R)
C190	547(R)	C191	195(R)	C192	196(R)	C193	197(R)
C194	198(R)	C195	199(R)	C196	200(R)	C197	201(R)
C198	202(R)	C199	203(R)	C200	204(R)	C201	205(R)
C202	206(R)	C203	207(R)	C204	208(R)	C205	209(R)
C206	210(R)	C207	211(R)	C208	212(R)	C209	213(R)
C210	214(R)	C211	215(R)	C212	216(R)	C213	217(R)
C214	218(R)	C215	219(R)	C216	220(R)	C217	221(R)
C218	222(R)	C219	223(R)	C220	224(R)	C221	225(R)
C222	226(R)	C223	227(R)	C224	228(R)	C225	229(R)
C226	230(R)	C227	231(R)	C228	232(R)	C229	233(R)
C230	234(R)	C231	235(R)	C232	236(R)	C233	237(R)
C234	238(R)	C235	239(R)	C236	240(R)	C237	241(R)
C238	242(R)	C239	243(R)	C240	244(R)	C241	245(R)
C242	246(R)	C243	247(R)	C244	248(R)	C245	249(R)
C246	250(R)	C247	251(R)	C248	252(R)	C249	253(R)
C250	254(R)	C251	255(R)	C252	256(R)	C253	257(R)
C254	258(R)	C255	259(R)	C256	260(R)	C257	261(R)
C258	262(R)	C259	263(R)	C260	264(R)	C261	265(R)
C262	266(R)	C263	267(R)	C264	268(R)	C265	269(R)
C266	270(R)	C267	271(R)	C268	272(R)	C269	273(R)
C270	274(R)	C271	275(R)	C272	276(R)	C273	277(R)
C274	278(R)	C275	279(R)	C276	280(R)	C277	281(R)
C278	282(R)	C279	283(R)	C280	284(R)	C281	285(R)
C282	286(R)	C283	287(R)	C284	288(R)	C285	289(R)
C286	290(R)	C287	291(R)	C288	292(R)	C289	293(R)
C290	294(R)	C291	295(R)	C292	296(R)	C293	297(R)
C294	298(R)	C295	299(R)	C296	300(R)	C297	301(R)
C298	302(R)	C299	303(R)	C300	304(R)	C301	305(R)
C302	306(R)	C303	307(R)	C304	308(R)	C305	309(R)
C306	310(R)	C307	311(R)	C308	312(R)	C309	313(R)
C310	314(R)	C311	315(R)	C312	316(R)	C313	317(R)
C314	318(R)	C315	319(R)	C316	320(R)	C317	321(R)
C318	322(R)	C319	323(R)	C320	324(R)	C321	325(R)
C322	326(R)	C323	327(R)	C324	328(R)	C325	329(R)
C326	330(R)	C327	331(R)	C328	332(R)	C329	333(R)
C330	334(R)	C331	335(R)	C332	336(R)	C333	337(R)
C334	338(R)	C335	339(R)	C336	340(R)	C337	341(R)
C338	342(R)	C339	343(R)	C340	344(R)	C341	345(R)
C342	346(R)	C343	347(R)	C344	348(R)	C345	349(R)
C346	350(R)	C347	351(R)	C348	352(R)	C349	353(R)
C350	354(R)	C351	355(R)	C352	356(R)	C353	357(R)
C354	358(R)	C355	359(R)	C356	360(R)	C357	361(R)
C358	362(R)	C359	363(R)	C360	364(R)	C361	365(R)
C362	366(R)	C363	367(R)	C364	368(R)	C365	369(R)
C366	370(R)	C367	371(R)	C368	372(R)	C369	373(R)
C370	374(R)	C371	375(R)	C372	376(R)	C373	377(R)
C374	378(R)	C375	379(R)	C376	380(R)	C377	381(R)
C378	382(R)	C379	383(R)	C380	384(R)	C381	385(R)
C382	386(R)	C383	387(R)	C384	388(R)	C385	389(R)
C386	390(R)	C387	391(R)	C388	392(R)	C389	393(R)
C390	394(R)	C391	395(R)	C392	396(R)	C393	397(R)
C394	398(R)	C395	399(R)	C396	400(R)	C397	401(R)
C398	402(R)	C399	403(R)	C400	404(R)	C401	405(R)
C402	406(R)	C403	407(R)	C404	408(R)	C405	409(R)
C406	410(R)	C407	411(R)	C408	412(R)	C409	413(R)
C410	414(R)	C411	415(R)	C412	416(R)	C413	417(R)
C414	418(R)	C415	419(R)	C416	420(R)	C417	421(R)
C418	422(R)	C419	423(R)	C420	424(R)	C421	425(R)
C422	426(R)	C423	427(R)	C424	428(R)	C425	429(R)
C426	430(R)	C427	431(R)	C428	432(R)	C429	438(R)
C430	439(R)	C431	503(R)	C432	441(R)	C433	442(R)
C434	443(R)	C435	444(R)	C436	445(R)	C437	446(R)
C438	447(R)	C439	448(R)	C440	449(R)	C441	450(R)
C442	451(R)	C443	452(R)	C444	453(R)	C445	454(R)
C446	455(R)	C447	456(R)	C448	457(R)	C449	458(R)
C450	459(R)	C451	460(R)	C452	461(R)	C453	462(R)
C454	463(R)	C455	464(R)	C456	465(R)	C457	466(R)
C458	467(R)	C459	468(R)	C460	469(R)	C461	508(R)
C462	471(R)	C463	472(R)	C464	473(R)	C465	474(R)
C466	475(R)	C467	476(R)	C468	477(R)	C469	478(R)
C470	533(R)	C471	542(R)	C472	481(R)	C473	482(R)
C474	483(R)	C475	484(R)	C476	543(R)	C477	486(R)
C478	487(R)	C479	488(R)	C480	489(R)	C481	490(R)
C482	491(R)	C483	492(R)	C484	493(R)	C485	692(R)
C486	495(R)	C487	496(R)	C488	497(R)	C489	498(R)
C490	499(R)	C491	500(R)	C492	501(R)	C493	502(R)
C494	504(R)	C495	505(R)	C496	506(R)	C497	507(R)
C498	509(R)	C499	510(R)	C500	511(R)	C501	512(R)
C502	513(R)	C503	514(R)	C504	515(R)	C505	516(R)
C506	517(R)	C507	518(R)	C508	519(R)	C509	520(R)
C510	521(R)	C511	522(R)	C512	523(R)	C513	524(R)
C514	525(R)	C515	526(R)	C516	527(R)	C517	528(R)
C518	529(R)	C519	530(R)	C520	531(R)	C521	532(R)
C522	534(R)	C523	535(R)	C524	536(R)	C525	537(R)
C526	538(R)	C527	539(R)	C528	540(R)	C529	541(R)
C530	544(R)	C531	545(R)	C532	730(R)	C1	1(R)
C533	881(R)	C534	885(R)	C535	919(R)

[0103] At the same time, it is found after several tests that the compounds and compositions of the present invention have good selectivity to many gramineae grasses such as zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and are able to control many important grass weeds and broad-leaved weeds. The compounds also show excellent selectivity and commercial value in the tests on sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods.

Claims

1. A carboxylic acid derivative-substituted iminoaryl compound, represented by general formula I' :

Q represents

Y represents halogen, haloalkyl or cyano;

Z represents halogen;

M represents CH or N;

X represents -CX₁X₂-(alkyl)_n-, -alkyl-CX₁X₂-(alkyl)_n- or -(CH₂)_r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkyl carbonyl, alkoxy carbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclic alkyl, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "cycloalkyl", "cycloalkylalkyl", "aryl", "heterocyclyl", "arylalkyl" and "heterocyclic alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

X₃ represents O, S, NH or N-alkyl;

Q₁, Q₂, Q₃, Q₄, Q₅ each independently represent O or S;

R₁, R₂ each independently represent H, cyano, alkyl, alkenyl, alkynyl, formyl alkyl, cyanoalkyl, amino, aminoalkyl, amino carbonyl, amino carbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl, R₄R₅N-(CO)-NR₃-,

, R₃-S(O)_m-(alkyl)_n-, R₃-O-(alkyl)_n-, R₃-(CO)-(alkyl)_n-, R₃-O-(alkyl)_n-(CO)-, R₃-(CO)-O-(alkyl)_n-, R3-S-(CO)-(alkyl)n-, R₃-O-(CO)-alkyl- or R₃-O-(CO)-O-alkyl-, wherein,

the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen,

the "amino", "aminoalkyl", "amino carbonyl", "amino carbonylalkyl" and "aminosulfonyl" are each independently unsubstituted or substituted by one or two groups selected from -R₁₁, -OR₁₁, -(CO)R₁₁, -(CO)OR₁₁, -alkyl-(CO)OR₁₁, -(SO₂)R₁₁, -(SO₂)OR₁₁, -alkyl-(SO₂)R₁₁, -(CO)N(R₁₂)₂ and -(SO₂)N(R₁₂)₂,

the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₆ represents alkyl, alkenyl, alkynyl or cyano, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, alkoxy and alkoxy carbonyl;

R₇, R₇', R₈, R₈' each independently represent H, alkyl, halogen, haloalkyl, amino, hydroxyalkyl or alkoxy;

R₃, R₄, R₅ each independently represent H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₁₁ independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, benzyl, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "phenyl" and "benzyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;

R₁₂ independently represents H, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or N(R₁₂)₂ in -(CO)N(R₁₂)₂ or -(SO₂)N(R₁₂)₂ each independently represents unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;

R₁₃ independently represents H, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy carbonyl, alkylthio, alkylsulfonyl, alkoxy and haloalkoxy;

r represents an integer of 2 or more; m represents 0, 1 or 2; n independently represents 0 or 1;

the derivative means that the carboxylic acid functional group in the general formula is changed into any ester, acylhydrazide, imidate, thioimidate, amidine, amide, orthoester, acyl cyanide, acyl halide, thioester, thionoester, dithiolester, nitrile or any other carboxylic acid derivative.

2. The carboxylic acid derivative-substituted iminoaryl compound according to claim 1, which is characterized in that the compound is represented by general formula I:

wherein, W represents OX₅, SX₅ or N(X₅)₂;

X₃, X₄ each independently represent O, S, NH or N-alkyl;

X₅ represents H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl,





wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, cycloalkenyl, heterocyclyl, aryl,



the "cycloalkyl", "cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

or unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position;

X₁₁ independently represents H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl, arylalkyl or

wherein, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, heterocyclyl, heterocyclic alkyl, aryl or arylalkyl, wherein, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "heterocyclyl", "heterocyclic alkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, alkoxy, alkoxyalkyl, alkyl carbonyl, alkoxy carbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenyl alkyl, aryl, arylalkyl, heterocyclyl or heterocyclic alkyl, or C, X₁₃, X₁₄, taken together, form unsubstituted or substituted cyclic structure, or N, X₁₃, X₁₄, taken together, form unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position, wherein, the "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted by halogen, the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenyl alkyl", "aryl", "arylalkyl", "heterocyclyl" and "heterocyclic alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-alkyl-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring.

3. The carboxylic acid derivative-substituted iminoaryl compound according to claim 1 or 2, which is characterized in that,

Y represents halogen, halo C1-C8 alkyl or cyano;

X represents -CX₁X₂-(C1-C8 alkyl)_n-, -(C1-C8 alkyl)-CX₁X₂-(C1-C8 alkyl)_n- or -(CH₂)_r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halo C1-C8 alkoxy, halo C1-C8 alkylthio, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkoxy C1-C8 alkyl, halo C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, aryl, heterocyclyl, aryl C1-C8 alkyl or heterocyclyl C1-C8 alkyl, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "aryl", "heterocyclyl", "aryl C1-C8 alkyl" and "heterocyclyl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

R₁, R₂ each independently represent H, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino, amino C1-C8 alkyl, amino carbonyl, amino carbonyl C1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, R₄R₅N-(CO)-NR₃-,

, R₃-S(O)_m-(C1-C8 alkyl)_n-, R₃-O-(C1-C8 alkyl)_n-, R₃-(CO)-(C1-C8 alkyl)n-, R₃-O-(C1-C8 alkyl)n-(CO)-, R₃-(CO)-O-(C1-C8 alkyl)n-, R₃-S-(CO)-(C1-C8 alkyl)n-, R₃-O-(CO)-(C1-C8 alkyl)- or R₃-O-(CO)-O-(C1-C8 alkyl)-, wherein,

the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen,

the "amino", "amino C1-C8 alkyl", "amino carbonyl", "amino carbonyl C1-C8 alkyl" and "aminosulfonyl" are each independently unsubstituted or substituted by one or two groups selected from -R₁₁, -OR₁₁, -(CO)R₁₁, -(CO)OR₁₁, -(C1-C8 alkyl)-(CO)OR₁₁, -(SO₂)R₁₁, -(SO₂)OR₁₁, -(C1-C8 alkyl)-(SO₂)R₁₁, -(CO)N(R₁₂)₂ and -(SO₂)N(R₁₂)₂,

the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₆ represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl or cyano, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkoxy and C1-C8 alkoxy carbonyl;

R₇, R₇', R₈, R₈' each independently represent H, C1-C8 alkyl, halogen, halo C1-C8 alkyl, amino, hydroxy C1-C8 alkyl or C1-C8 alkoxy;

R₃, R₄, R₅ each independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₁₁ independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, benzyl, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "phenyl" and "benzyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;

R₁₂ independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or N(R₁₂)₂ in -(CO)N(R₁₂)₂ or -(SO₂)N(R₁₂)₂ independently represents heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;

R₁₃ independently represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and halo C1-C8 alkoxy;

r represents 2, 3, 4, 5 or 6;

preferably, when the general formula is I, X₃, X₄ each independently represent O, S, NH or N-(C1-C8)alkyl;

X₅ represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl,



wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl,



the "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

with nitrogen atom at 1-position that is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl;

X₁₁ independently represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl or

wherein, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or C, X₁₃, X₁₄, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl, or N, X₁₃, X₁₄, taken together, form heterocyclyl with nitrogen atom at 1-position, wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl", "aryl C1-C8 alkyl", "heterocyclyl" and "heterocyclyl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C8 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring, the "5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl" is unsubstituted or substituted by 1-4 groups selected from C1-C8 alkyl, C1-C8 alkoxy carbonyl and benzyl, or together with aryl or heterocyclyl forms a fused ring, the "heterocyclyl with nitrogen atom at 1-position"is unsubstituted or substituted by at least one group selected from oxo and C1-C8 alkyl.

4. The carboxylic acid derivative-substituted iminoaryl compound according to claim 2 or 3, which is characterized in that,

Y represents halogen, halo C1-C6 alkyl or cyano;

X represents -CX₁X₂-(C1-C6 alkyl)_n-, -(C1-C6 alkyl)-CX₁X₂-(C1-C6 alkyl)n- or -(CH₂)r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C6 alkyl, halo C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, aryl, heterocyclyl, aryl C1-C6 alkyl or heterocyclyl C1-C6 alkyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "aryl", "heterocyclyl", "aryl C1-C6 alkyl" and "heterocyclyl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

R₁, R₂ each independently represent H, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino, amino C1-C6 alkyl, amino carbonyl, amino carbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, R₄R₅N-(CO)-NR₃-,

R₃-S(O)_m-(C1-C6 alkyl)_n-, R₃-O-(C1-C6 alkyl)_n-, R₃-(CO)-(C1-C6 alkyl)n-, R₃-O-(C1-C6 alkyl)n-(CO)-, R₃-(CO)-O-(C1-C6 alkyl)n-, R₃-S-(CO)-(C1-C6 alkyl)n-, R₃-O-(CO)-(C1-C6 alkyl)- or R₃-O-(CO)-O-(C1-C6 alkyl)-, wherein,

the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen,

the "amino", "amino C1-C6 alkyl", "amino carbonyl", "amino carbonyl C1-C6 alkyl" and "aminosulfonyl" are each independently unsubstituted or substituted by one or two groups selected from -R₁₁, -OR₁₁, -(CO)R₁₁, -(CO)OR₁₁, -(C1-C6 alkyl)-(CO)OR₁₁, -(SO₂)R₁₁, -(SO₂)OR₁₁, -(C1-C6 alkyl)-(SO₂)R₁₁, -(CO)N(R₁₂)₂ and -(SO₂)N(R₁₂)₂,

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₆ represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyano, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, C1-C6 alkoxy and C1-C6 alkoxy carbonyl;

R₇, R₇', R₈, R₈' each independently represent H, C1-C6 alkyl, halogen, halo C1-C6 alkyl, amino, hydroxy C1-C6 alkyl or C1-C6 alkoxy;

R₃, R₄, R₅ each independently represent H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

R₁₁ independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, benzyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "phenyl" and "benzyl"are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy;

R₁₂ independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or N(R₁₂)₂ in -(CO)N(R₁₂)₂ or -(SO₂)N(R₁₂)₂ independently represents heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

R₁₃ independently represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl or phenyl substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and halo C1-C6 alkoxy;

preferably, when the general formula is I, X₃, X₄ each independently represent O, S, NH or N-(C1-C6)alkyl;

X₅ represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,



wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,



the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

or heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

X₁₁ independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl or

wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, or C, X₁₃, X₁₄, taken together, form 5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl, or N, X₁₃, X₁₄, taken together, form heterocyclyl

with nitrogen atom at 1-position, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl", "aryl C1-C6 alkyl", "heterocyclyl" and "heterocyclyl C1-C6 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C6 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring, the "5~8 membered carbocyclyl or oxygen, sulfur or nitrogen-containing heterocyclyl" is unsubstituted or substituted by 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy carbonyl and benzyl, or together with aryl or heterocyclyl forms a fused ring, the



are unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl.

5. The carboxylic acid derivative-substituted iminoaryl compound according to any of claims 1 to 4, which is characterized in that,

X represents -CX₁X₂-(C1-C3 alkyl)_n-, -(C1-C3 alkyl)-CX₁X₂-(C1-C3 alkyl)n- or -(CH₂)r-;

X₁, X₂ each independently represent H, halogen, cyano, amino, nitro, formyl, cyano C1-C3 alkyl, hydroxy C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C3 alkyl, halo C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylamino C1-C3 alkyl, aryl, heterocyclyl, aryl C1-C3 alkyl or heterocyclyl C1-C3 alkyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "aryl", "heterocyclyl", "aryl C1-C3 alkyl" and "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring; and X₁, X₂ are not hydrogen at the same time;

preferably, when the general formula is I, X₅ represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,





, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl,



the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

or N(X₅)₂ represents

or heterocyclyl

with nitrogen atom at 1-position that is unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

X₁₁ independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl or

wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", "heterocyclyl C1-C3 alkyl", "aryl" and "aryl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₂ independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", "heterocyclyl C1-C3 alkyl", "aryl" and "aryl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring;

X₁₃, X₁₄ each independently represent H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or C, X₁₃, X₁₄, taken together, form 5~8 membered saturated carbocyclyl,

or

or N, X₁₃, X₁₄, taken together, form heterocyclyl

or

with nitrogen atom at 1-position, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted by halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl", "aryl C1-C3 alkyl", "heterocyclyl" and "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, -OR₁₃, -SR₁₃, -(CO)OR₁₃, -(SO₂)R₁₃, -N(R₁₃)₂ and -O-(C1-C3 alkyl)-(CO)OR₁₃, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted -OCH₂CH₂- or -OCH₂O- form a fused ring, the "5~8 membered saturated carbocyclyl,

is unsubstituted or substituted by 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy carbonyl and benzyl, or together with phenyl or thienyl forms a fused ring, the '

are unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl;

more preferably, Q represents

6. The carboxylic acid derivative-substituted iminoaryl compound according to any of claims 1 to 5, which is characterized in that, when the carbon atom connected to X₁ and X₂ in the general formula is a chiral center, it is in R configuration, and based on the content of stereoisomers having R and S configurations at this position, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), still more preferably 90-100% (R), further more preferably 95-100% (R); or preferably, it is any one selected from Table 1 and Table A.

7. A method for preparing the carboxylic acid derivative-substituted iminoaryl compound according to any of claims 1 to 6, which comprises the following steps:

subjecting a compound represented by general formula II and a compound represented by general formula III' to an elimination reaction to obtain a compound represented by general formula I', with the chemical reaction equation shown as follows:

or, subjecting a compound represented by general formula II and a compound represented by general formula III to an elimination reaction to obtain a compound represented by general formula I, with the chemical reaction equation shown as follows:

wherein, Hal represents halogen, other substituents Q, M, W, Y, Z, X, X₃ and X₄ are as defined in any of claims 1 to 6;

preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is at least one selected from inorganic bases and organic bases; more preferably, the solvent is at least one selected from DMF, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane and ethyl acetate.

8. A herbicidal composition, which is characterized in that, the composition comprises (i) at least one of the carboxylic acid derivative-substituted iminoaryl compounds according to any of claims 1 to 6 in a herbicidally effective amount; preferably, the composition further comprises (ii) one or more other herbicides in a herbicidally effective amount and/or safeners; more preferably, the composition further comprises (iii) a formulation auxiliary accepted in agricultural chemistry; still more preferably, the other herbicide is one or more selected from the following compounds and acids, salts and esters thereof:

(1) HPPD inhibitor selected from: topramezone, isoxaflutole, tembotrione, tefuryltrione, shuangzuocaotong, huanbifucaotong, sanzuohuangcaotong, benzuofucaotong and

(2) PDS inhibitor selected from: flurtamone, diflufenican and picolinafen;

(3) DOXP inhibitor selected from: clomazone and bixlozone;

(4) ALS inhibitor selected from: tribenuron-methyl, thifensulfuron methyl, pyrazosulfuron-ethyl, thiencarbazone-methyl, halosulfuron methyl, rimsulfuron, nicosulfuron and imazamox;

(5) ACCase inhibitor selected from: clethodim, sethoxydim and quizalofop-P-methyl;

(6) PPO inhibitor selected from: oxyfluorfen, oxadiazon, oxadiargyl, sulfentrazone, pyraclonil, flumioxazin, saflufenacil, carfentrazone-ethyl and trifludimoxazin;

(7) PSII inhibitor selected from: metribuzin, terbuthylazine, amicarbazone, chlorotoluron, isoproturon, bromacil, propanil, desmedipham, phenmedipham, bentazone and bromoxynil;

(8) inhibitor of microtubule assembly selected from: butralin and pendimethalin;

(9) VLCFA inhibitor selected from: butachlor, pretilachlor, mefenacet, s-metolachlor, flufenacet, pyroxasulfone and anilofos;

(10) lipid synthesis inhibitor (non-acetyl-CoA carboxylase): prosulfocarb;

(11) Synthetic hormones selected from:

fluroxypyr, florpyrauxifen benzyl, halauxifen-methyl, triclopyr, clopyralid, picloram, aminopyralid, dicamba, 2-methyl-4-chlorophenoxyacetic acid and 2,4-dichlorophenoxy acetic acid;

(12) EPSPS inhibitor: glyphosate;

(13) GS inhibitor selected from: glufosinate ammonium and glufosinate-P-ammonium;

(14) PSI inhibitor selected from: paraquat dichloride and diquat dibromide monohydrate;

(15) Cellulose synthesis inhibitor selected from: triaziflam and indaziflam;

(16) other herbicides: cinmethylin.

9. A method for controlling an undesirable plant, characterized in that it comprises applying at least one of the carboxylic acid derivative-substituted iminoaryl compounds according to any of claims 1 to 6 or the herbicidal composition according to claim 8 in a herbicidally effective amount on a plant or in its area or to soil or water to control the emergence or growth of undesirable plant; preferably, the undesirable plant includes herbicide-resistant or tolerant weed species.

10. Use of at least one of the carboxylic acid derivative-substituted iminoaryl compounds according to any of claims 1 to 6 or the herbicidal composition according to claim 8 for controlling a undesirable plant; preferably, the carboxylic acid derivative-substituted iminoaryl compound is used to control a weed in a useful crop, the useful crop is a genetically modified crop or a crop treated by genome editing technique, the weed includes herbicide-resistant or tolerant weed species.